(R)-4-[2-(Methyl­sulfanyl)pyrimidin-4-yl]-1-(tetra­hydro­furan-3-yl)-1H-pyrazol-5-amine

Liu, Z.; Liu, K.K.-C.; Elleraas, J.; Rheingold, A.L.; DiPasquale, A.; Yanovsky, A.

doi:10.1107/S160053680900734X

organic compounds

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Volume 65| Part 4| April 2009| Page o697

doi:10.1107/S160053680900734X

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(R)-4-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-(tetrahydrofuran-3-yl)-1H-pyrazol-5-amine

Zhengyu Liu,^a Kevin K.-C. Liu,^a Jeff Elleraas,^a Arnold L. Rheingold,^b Antonio DiPasquale ^b and Alex Yanovsky ^a ^*

^aPfizer Global Research and Development, La Jolla Labs, 10614 Science Center Drive, San Diego, CA 92121, USA, and ^bDepartment of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
^*Correspondence e-mail: alex.yanovsky@pfizer.com

(Received 26 February 2009; accepted 27 February 2009; online 6 March 2009)

The title compound, C₁₂H₁₅N₅OS, was obtained by reaction of 2-(2-(methylthio)pyrimidin-4-yl)-3-oxopropanenitrile with (tetrahydrofuran-3-yl)hydrazine dihydrochloride, and the racemic product was subsequently separated by chiral chromatography (first peak; [α]_D²⁰ = +51.3°). The chiral center at the substituted atom of the tetrahydrofuranyl group has an R-configuration. The pyrimidine and pyrazolyl rings are almost coplanar, their mean planes forming a dihedral angle of 6.4 (1)°. One of the H atoms of the amino group participates in an intramolecular hydrogen bond with the pyrimidine N atom in position 3. The second H atom is involved in an intermolecular hydrogen bond, which links the molecules into an infinite chain.

Related literature

For the structure of a related compound with a methyl-substituted amino group, see: Liu et al. (2009 ).

Experimental

Crystal data

C₁₂H₁₅N₅OS
M_r = 277.35
Orthorhombic, P 2₁ 2₁ 2
a = 15.479 (2) Å
b = 7.1217 (10) Å
c = 11.7802 (17) Å
V = 1298.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 208 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker D8 APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.844, T_max = 0.952
6570 measured reflections
3025 independent reflections
2844 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.115
S = 1.07
3025 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 1180 Friedel pairs
Flack parameter: −0.05 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N4ⁱ	0.87	2.19	2.9731 (19)	150
N3—H3B⋯N5	0.87	2.28	2.8616 (19)	124
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-32 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900734X/tk2382sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900734X/tk2382Isup2.hkl

checkCIF report

Comment top

The title compound was obtained by reaction of 2-(2-(methylthio)pyrimidin-4-yl)-3-oxopropanenitrile with (tetrahydrofuran-3-yl)hydrazine dihydrochloride. The racemic product was then separated with the help of chiral chromatography; the title compound, (I), was collected as the earlier fraction, when eluted with methanol using the Chiralpak column (99% ee; [α]_D²⁰ = +51.3°).

The present X-ray study unambiguously established the R configuration of the chiral center at the C3 atom (Fig. 1).

The pyrimidine and pyrazolyl rings lie approximately in one plane; the dihedral angle formed by their mean planes is equal to 6.4 (1)°. The orientation of the tetrahydrofurane ring can be characterized by the dihedral angle 99.6 (1)° formed by the pyrazolyl plane with the C2—C3—C4 plane.

The molecular geometry of (I) is similar to that of related compound with a methyl substituent at the amino group (Liu et al., 2009). However, the crystal packing is substantially different as (I) has one additional H atom capable of H-bond formation. Indeed, while the H3A atom forms an intramolecular H-bond with the N5 atom of the pyrimidine ring similar to that observed in methyl-substituted structure, the H3B atom is involved in intermolecular H-bonding, which links molecules into infinite chains running along the a axis (Fig. 2; Table 2).

Related literature top

For the structure of a related compound with a methyl-substituted amino group, see: Liu et al. (2009).

Experimental top

To a suspension of 2-(2-(methylthio)pyrimidin-4-yl)-3-oxopropanenitrile (13.5 g, 70.0 mmol) in AcOH (100 ml) was added (tetrahydrofuran-3-yl)hydrazine dihydrochloride (12.3 g,70.0 mmol), and the resulting orange mixture was heated at 80°C under nitrogen for 3 h. Acetic acid was removed and the orange solid residue was partitioned between aqueous Na₂CO₃ (200 ml) and EtOAc (400 ml). The mixture was refluxed for 30 min. The separated organic layer was washed with brine, dried over sodium sulfate and concentrated to give the crude product as a brown gum (16.82 g, 87%). The brown gum (8.32 g) was purified by flash chromatography using 30–70% EtOAc in hexane to afford a yellow solid (5.96 g).

The part of the product thus obtained (4.85 g) was subjected to chiral chromatography on Chiralpak AS—H 21.2 x 250 mm column with 35% MeOH in CO₂ at 140 bar as eluent (flow = 55 ml/min; UV detection at 260 nm). Two fractions corresponding to each of the enantiomers (Peak1 and Peak2) were collected and evaporated to dryness; the specific rotation [α]_D²⁰ was measured in CH₂Cl₂ solution and yielded the values of +51.3° and -52.1°, respectively. The enantiomer collected as Peak 1 was recrystallized from EtOAc/hexane to yield colorless single crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of (I), showing 50% probability displacement ellipsoids and atom numbering scheme. H atoms are drawn as circles with arbitrary small radius.
	Fig. 2. Crystal packing for (I) viewed down the b axis; H-bonds are shown as dashed lines.

(R)-4-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-(tetrahydrofuran-3-yl)- 1H-pyrazol-5-amine top

Crystal data top

C₁₂H₁₅N₅OS	F(000) = 584
M_r = 277.35	D_x = 1.419 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 5004 reflections
a = 15.479 (2) Å	θ = 2.6–28.1°
b = 7.1217 (10) Å	µ = 0.25 mm⁻¹
c = 11.7802 (17) Å	T = 208 K
V = 1298.6 (3) Å³	Block, yellow
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker D8 APEXII CCD area-detector diffractometer	3025 independent reflections
Radiation source: fine-focus sealed tube	2844 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
phi and ω scans	θ_max = 28.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→19
T_min = 0.844, T_max = 0.952	k = −4→9
6570 measured reflections	l = −15→13

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.0703P)² + 0.0815P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.115	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 0.24 e Å⁻³
3025 reflections	Δρ_min = −0.35 e Å⁻³
174 parameters	Extinction correction: SHELXL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.058 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1180 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.05 (8)

Crystal data top

C₁₂H₁₅N₅OS	V = 1298.6 (3) Å³
M_r = 277.35	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 15.479 (2) Å	µ = 0.25 mm⁻¹
b = 7.1217 (10) Å	T = 208 K
c = 11.7802 (17) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker D8 APEXII CCD area-detector diffractometer	3025 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2844 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.952	R_int = 0.043
6570 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.115	Δρ_max = 0.24 e Å⁻³
S = 1.07	Δρ_min = −0.35 e Å⁻³
3025 reflections	Absolute structure: Flack (1983), 1180 Friedel pairs
174 parameters	Absolute structure parameter: −0.05 (8)
0 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.61092 (15)	0.3862 (4)	1.04598 (18)	0.0592 (6)
H1A	0.6660	0.3550	1.0825	0.071*
H1B	0.5758	0.4600	1.0989	0.071*
C2	0.62567 (13)	0.4931 (3)	0.93597 (14)	0.0471 (4)
H2A	0.6760	0.5761	0.9418	0.057*
H2B	0.5748	0.5677	0.9154	0.057*
C3	0.64143 (10)	0.3354 (3)	0.85008 (15)	0.0414 (4)
H3	0.6054	0.3562	0.7818	0.050*
C4	0.61086 (12)	0.1571 (3)	0.91240 (18)	0.0514 (5)
H4A	0.5721	0.0835	0.8639	0.062*
H4B	0.6603	0.0785	0.9334	0.062*
C5	0.86860 (11)	0.3275 (3)	0.84766 (15)	0.0456 (4)
H5	0.9228	0.3341	0.8835	0.055*
C6	0.85782 (9)	0.3006 (3)	0.72974 (14)	0.0355 (4)
C7	0.76781 (9)	0.3006 (2)	0.71461 (13)	0.0341 (3)
C8	0.92276 (9)	0.2767 (2)	0.64376 (13)	0.0341 (3)
C9	1.01122 (10)	0.2623 (3)	0.66996 (14)	0.0427 (4)
H9	1.0308	0.2671	0.7454	0.051*
C10	1.06733 (10)	0.2412 (3)	0.58192 (16)	0.0466 (4)
H10	1.1264	0.2289	0.5987	0.056*
C11	0.95801 (10)	0.2531 (3)	0.45560 (14)	0.0371 (3)
C12	0.81445 (13)	0.2818 (3)	0.31648 (16)	0.0526 (5)
H12A	0.7888	0.1785	0.3583	0.079*
H12B	0.7917	0.2833	0.2398	0.079*
H12C	0.8006	0.3993	0.3539	0.079*
N1	0.73257 (8)	0.3241 (2)	0.81741 (12)	0.0393 (3)
N2	0.79452 (9)	0.3423 (3)	0.90197 (12)	0.0488 (4)
N3	0.72268 (9)	0.2815 (3)	0.61696 (12)	0.0493 (4)
H3A	0.6665	0.2841	0.6182	0.059*
H3B	0.7498	0.2667	0.5529	0.059*
N4	1.04322 (9)	0.2367 (3)	0.47231 (13)	0.0453 (4)
N5	0.89635 (8)	0.2704 (2)	0.53396 (11)	0.0341 (3)
O1	0.56646 (9)	0.2206 (3)	1.01145 (14)	0.0630 (5)
S1	0.92940 (3)	0.25258 (9)	0.31179 (4)	0.05191 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0580 (12)	0.0835 (15)	0.0362 (10)	0.0152 (11)	0.0142 (8)	0.0072 (10)
C2	0.0412 (9)	0.0661 (12)	0.0340 (8)	0.0096 (8)	0.0063 (7)	0.0034 (8)
C3	0.0248 (7)	0.0669 (11)	0.0325 (8)	0.0036 (7)	0.0002 (6)	0.0017 (8)
C4	0.0343 (8)	0.0675 (12)	0.0523 (11)	−0.0037 (8)	0.0026 (7)	0.0040 (10)
C5	0.0288 (7)	0.0790 (13)	0.0290 (7)	−0.0006 (8)	−0.0025 (6)	−0.0024 (8)
C6	0.0258 (7)	0.0512 (9)	0.0293 (7)	−0.0007 (6)	−0.0009 (5)	0.0000 (7)
C7	0.0269 (7)	0.0473 (8)	0.0282 (7)	0.0005 (6)	−0.0020 (5)	−0.0004 (6)
C8	0.0262 (6)	0.0443 (8)	0.0320 (7)	−0.0002 (6)	0.0010 (5)	0.0008 (6)
C9	0.0277 (7)	0.0655 (11)	0.0350 (7)	0.0007 (7)	−0.0029 (6)	0.0006 (9)
C10	0.0259 (7)	0.0684 (11)	0.0456 (9)	0.0031 (9)	0.0023 (6)	−0.0035 (9)
C11	0.0315 (7)	0.0471 (8)	0.0327 (7)	−0.0020 (7)	0.0027 (5)	−0.0045 (8)
C12	0.0438 (9)	0.0754 (13)	0.0385 (9)	0.0067 (9)	−0.0061 (7)	−0.0041 (10)
N1	0.0254 (6)	0.0642 (9)	0.0282 (6)	0.0003 (6)	−0.0011 (5)	−0.0007 (6)
N2	0.0290 (6)	0.0884 (12)	0.0290 (7)	−0.0003 (7)	−0.0043 (5)	−0.0034 (8)
N3	0.0284 (6)	0.0917 (13)	0.0278 (6)	0.0010 (7)	−0.0043 (5)	−0.0065 (8)
N4	0.0293 (6)	0.0657 (9)	0.0408 (7)	−0.0002 (7)	0.0045 (5)	−0.0076 (9)
N5	0.0287 (6)	0.0435 (7)	0.0300 (6)	−0.0016 (5)	0.0020 (4)	−0.0026 (6)
O1	0.0460 (8)	0.0826 (11)	0.0604 (9)	0.0041 (8)	0.0233 (6)	0.0185 (8)
S1	0.0394 (2)	0.0852 (4)	0.0311 (2)	−0.0016 (2)	0.00439 (15)	−0.0075 (2)

Geometric parameters (Å, º) top

C1—O1	1.425 (3)	C7—N1	1.339 (2)
C1—C2	1.520 (3)	C7—N3	1.353 (2)
C1—H1A	0.9800	C8—N5	1.357 (2)
C1—H1B	0.9800	C8—C9	1.407 (2)
C2—C3	1.531 (3)	C9—C10	1.361 (2)
C2—H2A	0.9800	C9—H9	0.9400
C2—H2B	0.9800	C10—N4	1.344 (2)
C3—N1	1.4644 (18)	C10—H10	0.9400
C3—C4	1.541 (3)	C11—N5	1.3334 (19)
C3—H3	0.9900	C11—N4	1.339 (2)
C4—O1	1.428 (3)	C11—S1	1.7510 (17)
C4—H4A	0.9800	C12—S1	1.792 (2)
C4—H4B	0.9800	C12—H12A	0.9700
C5—N2	1.317 (2)	C12—H12B	0.9700
C5—C6	1.412 (2)	C12—H12C	0.9700
C5—H5	0.9400	N1—N2	1.3888 (18)
C6—C7	1.4046 (19)	N3—H3A	0.8700
C6—C8	1.437 (2)	N3—H3B	0.8700

O1—C1—C2	104.11 (19)	N1—C7—C6	106.83 (13)
O1—C1—H1A	110.9	N3—C7—C6	128.32 (15)
C2—C1—H1A	110.9	N5—C8—C9	119.98 (14)
O1—C1—H1B	110.9	N5—C8—C6	117.70 (13)
C2—C1—H1B	110.9	C9—C8—C6	122.32 (14)
H1A—C1—H1B	109.0	C10—C9—C8	117.50 (15)
C1—C2—C3	102.70 (18)	C10—C9—H9	121.2
C1—C2—H2A	111.2	C8—C9—H9	121.2
C3—C2—H2A	111.2	N4—C10—C9	123.87 (14)
C1—C2—H2B	111.2	N4—C10—H10	118.1
C3—C2—H2B	111.2	C9—C10—H10	118.1
H2A—C2—H2B	109.1	N5—C11—N4	127.69 (15)
N1—C3—C2	111.55 (15)	N5—C11—S1	119.28 (12)
N1—C3—C4	112.07 (16)	N4—C11—S1	113.03 (12)
C2—C3—C4	103.93 (14)	S1—C12—H12A	109.5
N1—C3—H3	109.7	S1—C12—H12B	109.5
C2—C3—H3	109.7	H12A—C12—H12B	109.5
C4—C3—H3	109.7	S1—C12—H12C	109.5
O1—C4—C3	106.03 (18)	H12A—C12—H12C	109.5
O1—C4—H4A	110.5	H12B—C12—H12C	109.5
C3—C4—H4A	110.5	C7—N1—N2	112.28 (13)
O1—C4—H4B	110.5	C7—N1—C3	129.58 (14)
C3—C4—H4B	110.5	N2—N1—C3	118.13 (13)
H4A—C4—H4B	108.7	C5—N2—N1	104.20 (14)
N2—C5—C6	112.69 (15)	C7—N3—H3A	120.0
N2—C5—H5	123.7	C7—N3—H3B	120.0
C6—C5—H5	123.7	H3A—N3—H3B	120.0
C7—C6—C5	104.00 (14)	C11—N4—C10	114.37 (14)
C7—C6—C8	127.19 (14)	C11—N5—C8	116.57 (13)
C5—C6—C8	128.81 (14)	C1—O1—C4	105.25 (15)
N1—C7—N3	124.85 (14)	C11—S1—C12	102.76 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N4ⁱ	0.87	2.19	2.9731 (19)	150
N3—H3B···N5	0.87	2.28	2.8616 (19)	124

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅N₅OS
M_r	277.35
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	208
a, b, c (Å)	15.479 (2), 7.1217 (10), 11.7802 (17)
V (Å³)	1298.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker D8 APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.844, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	6570, 3025, 2844
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.663

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.115, 1.07
No. of reflections	3025
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.35
Absolute structure	Flack (1983), 1180 Friedel pairs
Absolute structure parameter	−0.05 (8)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-32 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N4ⁱ	0.87	2.19	2.9731 (19)	149.5
N3—H3B···N5	0.87	2.28	2.8616 (19)	124.4

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, Z., Liu, K. K.-C., Elleraas, J., Rheingold, A. L., DiPasquale, A. & Yanovsky, A. (2009). Acta Cryst. E65, o616. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o697

doi:10.1107/S160053680900734X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(R)-4-[2-(Methyl­sulfanyl)pyrimidin-4-yl]-1-(tetra­hydro­furan-3-yl)-1H-pyrazol-5-amine

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Experimental

Crystal data

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Refinement

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organic compounds

(R)-4-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-(tetrahydrofuran-3-yl)-1H-pyrazol-5-amine