(R)-N-Methyl-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/S1600536809006369

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o616

doi:10.1107/S1600536809006369

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(R)-N-Methyl-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 19 February 2009; accepted 20 February 2009; online 28 February 2009)

The chiral center at the substituted atom of the tetrahydrofuranyl ring in the title compound, C₁₃H₁₇N₅OS, has an R configuration. The methylsulfanylpyrimidine group and the pyrazole ring are almost coplanar [the maximum deviation from this plane is 0.070 (4) Å], the N—Me substituent being displaced from the methylsulfanylpyrimidine-pyrazole plane by 0.880 (4) Å. The secondary amine group participates in an intramolecular hydrogen bond with the pyrimidine N atom in position 3.

Related literature

For the structures of related pyrimidine derivatives with similar intramolecular hydrogen bonds, see: Golic et al. (1993 ).

Experimental

Crystal data

C₁₃H₁₇N₅OS
M_r = 291.38
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.6209 (4) Å
b = 14.0757 (9) Å
c = 14.6793 (10) Å
V = 1368.02 (15) Å³
Z = 4
Cu Kα radiation
μ = 2.14 mm⁻¹
T = 100 K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.783, T_max = 0.882
9765 measured reflections
2419 independent reflections
2388 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.057
S = 1.06
2419 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 964 Friedel pairs
Flack parameter: 0.061 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N5	0.858 (15)	2.157 (15)	2.8510 (14)	137.9 (14)

Data collection: APEX2 (Bruker–Nonius, 2004 ); cell refinement: SAINT (Bruker–Nonius, 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/S1600536809006369/tk2375sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006369/tk2375Isup2.hkl

checkCIF report

Comment top

The title compound (I) was obtained by N-methylation of 4-(2-(methylsulfanyl)pyrimidin-4-yl)-1-(tetrahydrofuran-2-yl)-1H-pyrazol-5-amine with methyl iodide. The racemic product was then separated with the help of chiral chromatography; (I) was collected as the earlier fraction when eluted with isopropyl alcohol using the Chiralpak column (99% ee; [α]_D²⁰ = -191.4°)

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

The methylsulfanylpyrimidine group and pyrazolyl ring lie approximately in one plane. The maximum deviation from this plane being 0.070 (4) Å for the C13 atom; the displacement of methyl-C8 atom from this plane is 0.880 (4) Å. The orientation of the tetrahydrofuran ring can be characterized by the dihedral angle of 98.1 (3)° formed by the pyrimidine-pyrazolyl plane with the C2—C3—C4 plane.

The secondary amino group forms an intramolecular hydrogen bond with the N5 atom of the pyrimidine ring, Table 1, the geometry of this bond is similar to that observed in ethyl (Z)-2-amino-3-(4-pyrimidinyl)propenoate (Golic et al., 1993).

Related literature top

For the structures of related pyrimidine derivatives with similar intramolecular hydrogen bonds, see: Golic et al. (1993).

Experimental top

A solution of -(2-(methylsulfanyl)pyrimidin-4-yl)-1-(tetrahydrofuran-2-yl)-1H-pyrazol-5-amine (8.32 g, 30.0 mmol) in anhydrous THF (80 ml) was added dropwise to a suspension of hexane-washed NaH (60% dispersion in mineral oil, 1.92 g, 48.0 mmol) in anhydrous THF (20 ml) at room temperature. The resulting orange reaction mixture was stirred under nitrogen for 30 minutes; thereafter MeI (5.96 g, 42.0 mmol) was added dropwise. The reaction mixture was stirred at room temperature under nitrogen overnight and then quenched with aqueous NH₄Cl (100 ml). EtOAc (200 ml) was added and layers were separated. The organic extract was washed with brine, dried over sodium sulfate, and concentrated to give the crude product, which was purified by flash chromatography using 20–50% EtOAc in hexane to afford 5.85 g (67%) of yellow solid. The racemic product thus obtained was subjected to chiral chromatography on Chiralpak AS—H 21.2 x 250 mm column with 15% IPA in CO₂ at 140 bar as eluent (temp = 35°C; flow = 60 ml/min; UV detection at 260 nm). Two fractions corresponding to each of the enantiomers (Peak1 and Peak2) were collected and evaporated to dryness; specific rotation [α]_D²⁰ was measured in methanol solution and yielded the values of -191.4° and +224.1°, respectively. The enantiomer collected as Peak 1 was recrystallized from EtOAc/hexane to yield single crystals.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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.

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

Crystal data top

C₁₃H₁₇N₅OS	F(000) = 616
M_r = 291.38	D_x = 1.415 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8684 reflections
a = 6.6209 (4) Å	θ = 3.1–68.1°
b = 14.0757 (9) Å	µ = 2.14 mm⁻¹
c = 14.6793 (10) Å	T = 100 K
V = 1368.02 (15) Å³	Block, colorless
Z = 4	0.12 × 0.10 × 0.06 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2419 independent reflections
Radiation source: fine-focus sealed tube	2388 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 67.9°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
T_min = 0.783, T_max = 0.882	k = −16→16
9765 measured reflections	l = −11→17

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.021	w = 1/[σ²(F_o²) + (0.0319P)² + 0.2281P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.057	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.22 e Å⁻³
2419 reflections	Δρ_min = −0.16 e Å⁻³
187 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0024 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 964 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.061 (12)

Crystal data top

C₁₃H₁₇N₅OS	V = 1368.02 (15) Å³
M_r = 291.38	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 6.6209 (4) Å	µ = 2.14 mm⁻¹
b = 14.0757 (9) Å	T = 100 K
c = 14.6793 (10) Å	0.12 × 0.10 × 0.06 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2419 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2388 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.882	R_int = 0.021
9765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.057	Δρ_max = 0.22 e Å⁻³
S = 1.06	Δρ_min = −0.16 e Å⁻³
2419 reflections	Absolute structure: Flack (1983), 964 Friedel pairs
187 parameters	Absolute structure parameter: 0.061 (12)
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	0.4029 (2)	0.30990 (12)	0.04871 (10)	0.0272 (3)
H1A	0.4395	0.2446	0.0676	0.033*
H1B	0.3269	0.3069	−0.0093	0.033*
C2	0.2806 (2)	0.35928 (10)	0.12196 (10)	0.0213 (3)
H2A	0.1860	0.3147	0.1519	0.026*
H2B	0.2034	0.4134	0.0966	0.026*
C3	0.4445 (2)	0.39343 (9)	0.18853 (8)	0.0167 (3)
H3	0.4133	0.4595	0.2093	0.020*
C4	0.6387 (2)	0.39367 (10)	0.12981 (10)	0.0214 (3)
H4A	0.7017	0.4575	0.1302	0.026*
H4B	0.7375	0.3472	0.1539	0.026*
C5	0.4646 (2)	0.19552 (9)	0.33361 (8)	0.0149 (3)
H5	0.4649	0.1289	0.3441	0.018*
C6	0.4610 (2)	0.26374 (9)	0.40411 (9)	0.0138 (3)
C7	0.4621 (2)	0.35123 (9)	0.35763 (8)	0.0135 (2)
C8	0.5746 (2)	0.52007 (10)	0.36114 (10)	0.0215 (3)
H8A	0.6704	0.4970	0.3153	0.032*
H8B	0.6490	0.5481	0.4122	0.032*
H8C	0.4865	0.5682	0.3338	0.032*
C9	0.4629 (2)	0.24930 (9)	0.50139 (9)	0.0135 (3)
C10	0.4728 (2)	0.15830 (9)	0.54074 (9)	0.0162 (3)
H10	0.4773	0.1026	0.5042	0.019*
C11	0.4755 (2)	0.15340 (9)	0.63402 (9)	0.0159 (3)
H11	0.4826	0.0924	0.6615	0.019*
C12	0.4595 (2)	0.31224 (9)	0.64505 (8)	0.0136 (2)
C13	0.4376 (2)	0.37321 (10)	0.82303 (9)	0.0210 (3)
H13A	0.3289	0.3262	0.8275	0.032*
H13B	0.4109	0.4256	0.8654	0.032*
H13C	0.5666	0.3432	0.8386	0.032*
N1	0.46330 (18)	0.33043 (7)	0.26754 (7)	0.0148 (2)
N2	0.46738 (18)	0.23371 (7)	0.25178 (8)	0.0166 (2)
N3	0.4520 (2)	0.44067 (7)	0.39416 (7)	0.0171 (2)
N4	0.46873 (18)	0.22994 (7)	0.68912 (7)	0.0153 (2)
N5	0.45642 (17)	0.32731 (7)	0.55510 (7)	0.0142 (2)
O1	0.57971 (18)	0.36833 (9)	0.03959 (7)	0.0318 (3)
S1	0.44904 (5)	0.41854 (2)	0.70856 (2)	0.01652 (9)
H3N	0.456 (3)	0.4369 (11)	0.4524 (10)	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0362 (9)	0.0310 (8)	0.0143 (7)	−0.0093 (7)	−0.0007 (6)	−0.0027 (6)
C2	0.0218 (7)	0.0245 (7)	0.0178 (7)	−0.0019 (6)	−0.0048 (6)	0.0038 (6)
C3	0.0195 (6)	0.0169 (6)	0.0136 (6)	0.0011 (6)	−0.0012 (6)	0.0028 (5)
C4	0.0232 (7)	0.0236 (7)	0.0173 (7)	−0.0037 (6)	0.0020 (6)	0.0017 (6)
C5	0.0144 (6)	0.0143 (6)	0.0160 (6)	0.0004 (6)	0.0003 (6)	−0.0005 (5)
C6	0.0117 (6)	0.0151 (6)	0.0146 (6)	−0.0003 (5)	0.0006 (6)	0.0005 (5)
C7	0.0099 (5)	0.0168 (6)	0.0139 (6)	0.0004 (5)	0.0020 (6)	0.0000 (5)
C8	0.0249 (8)	0.0185 (6)	0.0212 (7)	−0.0053 (6)	0.0008 (6)	0.0003 (5)
C9	0.0082 (6)	0.0170 (6)	0.0154 (6)	−0.0009 (5)	−0.0003 (6)	−0.0002 (5)
C10	0.0150 (6)	0.0153 (6)	0.0183 (6)	0.0006 (6)	−0.0001 (6)	0.0003 (5)
C11	0.0131 (6)	0.0156 (6)	0.0190 (6)	−0.0003 (5)	−0.0002 (6)	0.0036 (5)
C12	0.0096 (6)	0.0158 (6)	0.0154 (6)	−0.0008 (6)	−0.0005 (6)	0.0004 (5)
C13	0.0287 (8)	0.0208 (7)	0.0137 (6)	−0.0034 (6)	0.0004 (6)	0.0009 (5)
N1	0.0183 (5)	0.0138 (5)	0.0122 (5)	0.0015 (5)	0.0001 (5)	0.0010 (4)
N2	0.0186 (5)	0.0137 (5)	0.0176 (5)	0.0017 (5)	0.0003 (5)	−0.0018 (4)
N3	0.0240 (6)	0.0136 (5)	0.0137 (5)	−0.0014 (5)	0.0036 (5)	0.0002 (4)
N4	0.0135 (5)	0.0160 (5)	0.0164 (5)	0.0004 (5)	−0.0007 (5)	0.0017 (4)
N5	0.0136 (5)	0.0149 (5)	0.0141 (5)	−0.0005 (5)	0.0010 (5)	0.0013 (4)
O1	0.0363 (6)	0.0441 (7)	0.0152 (5)	−0.0122 (5)	0.0067 (5)	−0.0030 (5)
S1	0.02089 (16)	0.01483 (15)	0.01383 (15)	−0.00088 (14)	−0.00033 (14)	0.00007 (12)

Geometric parameters (Å, º) top

C1—O1	1.4369 (18)	C8—N3	1.4639 (17)
C1—C2	1.515 (2)	C8—H8A	0.9800
C1—H1A	0.9900	C8—H8B	0.9800
C1—H1B	0.9900	C8—H8C	0.9800
C2—C3	1.5373 (19)	C9—N5	1.3525 (17)
C2—H2A	0.9900	C9—C10	1.4066 (18)
C2—H2B	0.9900	C10—C11	1.3710 (18)
C3—N1	1.4652 (15)	C10—H10	0.9500
C3—C4	1.5484 (19)	C11—N4	1.3479 (17)
C3—H3	1.0000	C11—H11	0.9500
C4—O1	1.4262 (18)	C12—N4	1.3282 (16)
C4—H4A	0.9900	C12—N5	1.3375 (16)
C4—H4B	0.9900	C12—S1	1.7644 (13)
C5—N2	1.3162 (16)	C13—S1	1.7990 (13)
C5—C6	1.4119 (17)	C13—H13A	0.9800
C5—H5	0.9500	C13—H13B	0.9800
C6—C7	1.4080 (17)	C13—H13C	0.9800
C6—C9	1.4425 (17)	N1—N2	1.3811 (14)
C7—N1	1.3545 (16)	N3—H3N	0.858 (15)
C7—N3	1.3700 (16)

O1—C1—C2	103.83 (12)	N3—C8—H8B	109.5
O1—C1—H1A	111.0	H8A—C8—H8B	109.5
C2—C1—H1A	111.0	N3—C8—H8C	109.5
O1—C1—H1B	111.0	H8A—C8—H8C	109.5
C2—C1—H1B	111.0	H8B—C8—H8C	109.5
H1A—C1—H1B	109.0	N5—C9—C10	120.10 (12)
C1—C2—C3	102.56 (12)	N5—C9—C6	117.54 (11)
C1—C2—H2A	111.3	C10—C9—C6	122.36 (12)
C3—C2—H2A	111.3	C11—C10—C9	117.16 (12)
C1—C2—H2B	111.3	C11—C10—H10	121.4
C3—C2—H2B	111.3	C9—C10—H10	121.4
H2A—C2—H2B	109.2	N4—C11—C10	123.96 (12)
N1—C3—C2	111.96 (11)	N4—C11—H11	118.0
N1—C3—C4	111.79 (11)	C10—C11—H11	118.0
C2—C3—C4	103.48 (10)	N4—C12—N5	128.31 (12)
N1—C3—H3	109.8	N4—C12—S1	118.95 (9)
C2—C3—H3	109.8	N5—C12—S1	112.74 (9)
C4—C3—H3	109.8	S1—C13—H13A	109.5
O1—C4—C3	106.78 (12)	S1—C13—H13B	109.5
O1—C4—H4A	110.4	H13A—C13—H13B	109.5
C3—C4—H4A	110.4	S1—C13—H13C	109.5
O1—C4—H4B	110.4	H13A—C13—H13C	109.5
C3—C4—H4B	110.4	H13B—C13—H13C	109.5
H4A—C4—H4B	108.6	C7—N1—N2	112.13 (10)
N2—C5—C6	113.04 (11)	C7—N1—C3	129.90 (11)
N2—C5—H5	123.5	N2—N1—C3	117.75 (10)
C6—C5—H5	123.5	C5—N2—N1	104.45 (10)
C7—C6—C5	103.86 (11)	C7—N3—C8	123.02 (12)
C7—C6—C9	127.08 (12)	C7—N3—H3N	109.4 (10)
C5—C6—C9	129.03 (12)	C8—N3—H3N	111.1 (11)
N1—C7—N3	125.53 (11)	C12—N4—C11	113.97 (11)
N1—C7—C6	106.50 (11)	C12—N5—C9	116.49 (11)
N3—C7—C6	127.87 (11)	C4—O1—C1	106.25 (11)
N3—C8—H8A	109.5	C12—S1—C13	101.21 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N5	0.858 (15)	2.157 (15)	2.8510 (14)	137.9 (14)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇N₅OS
M_r	291.38
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.6209 (4), 14.0757 (9), 14.6793 (10)
V (Å³)	1368.02 (15)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.14
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.783, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	9765, 2419, 2388
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.057, 1.06
No. of reflections	2419
No. of parameters	187
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.16
Absolute structure	Flack (1983), 964 Friedel pairs
Absolute structure parameter	0.061 (12)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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—H3N···N5	0.858 (15)	2.157 (15)	2.8510 (14)	137.9 (14)

References

Bruker–Nonius (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SADABS. 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
Golic, L., Sinur, A. & Tisler, M. (1993). Acta Chim. Slov. 40, 281–288. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o616

doi:10.1107/S1600536809006369

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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