6-Amino-2,5-bis(pivaloylamino)pyrimidin-4(3H)-one dihydrate

Abstract

The asymmetric unit of the title compound, C14H23N5O3·2H2O, contains two crystallographically independent 6-amino-2,5-bis­(pivaloylamino)pyrimidin-4(3H)-one mol­ecules (A and B) with similar geometry and four water mol­ecules. In both independent mol­ecules, one of the amide groups is almost coplanar with the pyrimidine ring [dihedral angle of 12.85 (9) in A and 12.30 (10)° in B], whereas the other amide group is significantly twisted away from it [dihedral angle is 72.18 (7) in A and 71.29 (7)° in B]. In each independent mol­ecule, an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. Mol­ecules A and B are linked into chains along the a axis by N—H⋯O and C—H⋯O hydrogen bonds. Adjacent chains are linked into a two-dimensional network parallel to the ac plane by water mol­ecules via N—H⋯O and O—H⋯O hydrogen bonds.

Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-methoxypyrimidine-4-carboxylate

“…The result showed that the title compound was the byproduct of the reaction. The pyrimidinone ring is planar, as it is in a related compound (Fun et al, 2009). This is in contrast with another related compound (Shang et al, 2007), where the heterocyclic ring is twisted.…”

“…For background to raltegravir, see: Steigbigel et al (2008). For related structures, see: Shang & Shang (2007); Fun et al (2009). Mo K radiation = 0.11 mm À1 T = 113 K 0.20 Â 0.16 Â 0.12 mm…”