Received 13 August 2009
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) plane.
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 ).
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.