Research Article: 6-(3,5-Dimethyl­benz­yl)-5-ethyl-1-[(2-phenyl­eth­oxy)meth­yl]pyrimidine-2,4(1H,3H)dione

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Nasser R. El-Brollosy, Mohamed I. Attia, Hazem A. Ghabbour, Suchada Chantrapromma, Hoong-Kun Fun.


In the title pyrimidine derivative, C24H28N2O3, the uracil unit is essentially planar with an r.m.s. deviation of 0.0054 (1) Å for the eight non-H atoms. The pyrimidine ring is tilted by a dihedral angle of 77.08 (7)° with respect to the aromatic ring of the 3,5-dimethyl­benzyl substituent, whereas it is nearly parallel to the benzene ring of the pheneth­oxy­methyl unit, with a dihedral angle of 8.17 (8)°. An intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by a pair of amide–uracil N—H⋯O hydrogen bonds into an inversion R22(8) dimer. These dimers are stacked along the b axis through π–π inter­actions with a centroid–centroid distance of 3.9517 (8) Å. Weak C—H⋯π inter­actions are also present.

Partial Text

For bond-length data, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to anti-viral HIV therapies, see: El-Brollosy et al. (2007 ▶, 2008 ▶, 2009 ▶); Hopkins et al. (1996 ▶, 1999 ▶). For related structures, see: El-Brollosy et al. (2011 ▶, 2012 ▶).