1-(4-tert-Butyl­benz­yl)pyrimidine-2,4(1H,3H)-dione

Hong-Sheng Wang; Gong-Chun Li

doi:10.1107/S1600536812008999

. 2012 Mar 14;68(Pt 4):o1047. doi: 10.1107/S1600536812008999

1-(4-tert-Butylbenzyl)pyrimidine-2,4(1H,3H)-dione

Hong-Sheng Wang ^a,^*, Gong-Chun Li ^a

PMCID: PMC3344008 PMID: 22589917

Abstract

The asymmetric unit of the title compound, C₁₅H₁₈N₂O₂, contains two independent molecules with essentially identical geometries and conformations. The dihedral angles between the benzene and pyrimidine rings in the two molecules are 89.96 (11) and 73.91 (11)°. The six methyl groups are disordered over two sets of sites, with site occupancies of 0.545 (4):0.455 (4) and 0.542 (7):0.458 (7) in the two molecules. The crystal structure is stabilized by N—H⋯O hydrogen bonds.

Related literature

For the bioactivity of pyrimidine-2,4(1H,3H)-diones, see: Konz (1997 ▶); Reinhard et al. (2004 ▶); Komori & Sanemitsu (2002 ▶); Radatus & Karimian (1993 ▶); Starrett et al. (1992 ▶). For a related structure, see: Li et al. (2005 ▶).

Experimental

Crystal data

C₁₅H₁₈N₂O₂
M _r = 258.31
Monoclinic,
a = 20.853 (7) Å
b = 10.013 (4) Å
c = 13.893 (5) Å
β = 94.915 (6)°
V = 2890.2 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 K
0.40 × 0.28 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T _min = 0.969, T _max = 0.984
14804 measured reflections
5292 independent reflections
2946 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.207
S = 1.02
5292 reflections
351 parameters
186 restraints
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008999/fj2505sup1.cif

e-68-o1047-sup1.cif^{(37.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008999/fj2505Isup2.hkl

e-68-o1047-Isup2.hkl^{(259.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008999/fj2505Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	2.06	2.915 (3)	174
N3—H3⋯O4ⁱⁱ	0.86	2.03	2.851 (3)	160

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the Natural Science Foundation of Henan Province China (grant No. 082300420110) and the Natural Science Foundation of Henan Province Eduation Department, China (grant No. 2007150036).

supplementary crystallographic information

Comment

Derivatives of pyrimidine-2,4(1H,3H)-dione are very important molecules in biology and have many application in the areas of herbicide (Konz, 1997; Reinhard et al., 2004; Komori and Sanemitsu 2002). Derivatives of pyrimidine-2,4(1H,3H)-dione have also been developed as antiviral agents, shch as AZT which is the most widely used anti-AIDS drug (Radatus & Karimian, 1993) and stavudine which is the most widely used anti-HIV drug (Starrett et al., 1992). In order to discover further biologically active pyrimidine compounds, the title compound, (I), was synthesized and its crystal structure determined (Fig. 1).

In the crystal structure of the title molecule, The asymmetric unit contains two independent molecules, with essentially identical geometries and conformations. The dihedral angles between the benzene rings and the pyrimidine rings in the two molecules are 89.96 (0.11) and 73.91 (0.11)°. The six methyl groups are disordered over two positions, with site-occupancies of 0.545 (4):0.455 (4) and 0.542 (7):0.458 (7) in the two molecules. The crystal structure is stabilized by N—H···O hydrogen bonds. For a crystal structure related to the title compound, see: Li et al. (2005).

Experimental

Uracil (0.56 g, 5 mmol) and anhydrous potassium carbonate (0.84 g, 6 mmol) were mixed in N,N-dimethylformamide (20 ml). A solution of 4-tertbutylbenzyl chloride (0.92 g, 5 mmol) in acetone (10 ml) was then added dropwise, with stirring, at room temperature, and the mixture was stirred for another 10 h and then refluxed for 4 h. The solvent was evaporated in vacuo and the residue was washed with water. The resulting white precipitate was filtered off and purified by column chromatography on silica gel (petroleum ether:ethyl acetate = 2:1). The title compound was recrystallized from ethanol and single crystals of (I) were obtained.