trans-4-(2-Amino-5-bromo-6-methyl­pyrimidin-4-ylamino)-1-methyl­cyclo­hexa­nol

Hoffman, J.E.; Cheng, H.; Rheingold, A.L.; DiPasquale, A.; Yanovsky, A.

doi:10.1107/S1600536809035533

Volume 65
Part 10
Page o2374
October 2009

Received 13 August 2009
Accepted 2 September 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 198 K
Mean (C-C) = 0.004 Å
R = 0.041
wR = 0.114
Data-to-parameter ratio = 19.6
Details

trans-4-(2-Amino-5-bromo-6-methylpyrimidin-4-ylamino)-1-methylcyclohexanol

Jacqui E. Hoffman,^a Henry Cheng,^a Arnold L. Rheingold,^b Antonio DiPasquale ^b and Alex Yanovsky ^a ^*

^aPfizer Global Research and Development, La Jolla Labs, 10770 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

The title compound, C₁₂H₁₉BrN₄O, represents the minor component of the two products obtained in a series of transformations involving the Grignard reaction of tert-butoxycarbonyl-protected 4-aminocyclohexanone with MeMgBr, and subsequent interaction of the obtained amino-substituted cyclohexanol with 4-chloro-6-methylpyrimidin-2-amine followed by bromination with N-bromosuccinimide. The X-ray structure showed that this product represents a trans isomer with respect to the amino and hydroxy substituents in the cyclohexyl ring; the dihedral angle between the aminopyrimidine plane and the (noncrystallographic) mirror plane of the substituted cyclohexyl fragment is 33.6 (3)°. Only two of the four potentially `active' H atoms participate in intermolecular N-HO and O-HN hydrogen bonds, linking the molecules into layers parallel to the (10 $[\overline{1}]$ ) plane.

Related literature

For the structure of a similar N-pyrimidine derivative of aminocyclohexane, see Melguizo et al. (2003).

Experimental

Crystal data

C₁₂H₁₉BrN₄O
M_r = 315.22
Monoclinic, P 2₁ /n
a = 9.9514 (18) Å
b = 7.1879 (11) Å
c = 19.566 (4) Å
= 91.053 (3)°
V = 1399.3 (4) Å³
Z = 4
Mo K radiation
= 2.93 mm^-1
T = 198 K
0.10 × 0.10 × 0.08 mm

Data collection

Siemens P4 with APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.758, T_max = 0.799
8853 measured reflections
3251 independent reflections
2500 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.114
S = 1.05
3251 reflections
166 parameters
H-atom parameters constrained
_max = 0.83 e Å^-3
_min = -0.77 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO1ⁱ	0.88	2.03	2.828 (3)	151
O1-H1N1ⁱⁱ	0.84	2.02	2.803 (3)	155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2293 ).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Melguizo, M., Quesada, A., Low, J. N. & Glidewell, C. (2003). Acta Cryst. B59, 263-276.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds