2-[(2-Meth­oxy­eth­yl)sulfan­yl]-4-(2-methyl­prop­yl)-6-oxo-1,6-dihydro­pyrimidine-5-carbonitrile

Ali A El-Emam; Güneş Demirtaş; Necmi Dege; Omar A Al-Deeb; Nasser R El-Brollosy

doi:10.1107/S1600536812013372

. 2012 Apr 13;68(Pt 5):o1379. doi: 10.1107/S1600536812013372

2-[(2-Methoxyethyl)sulfanyl]-4-(2-methylpropyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Ali A El-Emam ^a, Güneş Demirtaş ^b, Necmi Dege ^b,^*, Omar A Al-Deeb ^a, Nasser R El-Brollosy ^a

PMCID: PMC3344508 PMID: 22590270

Abstract

In the title compound, C₁₂H₁₇N₃O₂S, the 4-methyl-2-methylsulfanyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile part of the molecule is almost planar (r.m.s deviation = 0.062 Å). In the crystal, molecules form centrosymmetric dimers via pairs of N—H⋯O hydrogen bonds.

Related literature

For related pyrimidine structures, see: Yan et al. (2011 ▶); El-Brollosy et al. (2011 ▶); Nasir et al. (2010 ▶); Tiekink (1989 ▶); Al-Deeb et al. (2012 ▶); Durkaya et al. (2011 ▶).

Experimental

Crystal data

C₁₂H₁₇N₃O₂S
M _r = 267.35
Triclinic,
a = 5.0379 (5) Å
b = 10.5453 (10) Å
c = 13.3936 (13) Å
α = 85.274 (8)°
β = 82.170 (8)°
γ = 83.034 (8)°
V = 698.14 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.68 × 0.47 × 0.15 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.859, T _max = 0.966
6663 measured reflections
2725 independent reflections
2090 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.126
S = 1.02
2725 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: WinGX (Farrugia, 1997 ▶) and SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013372/bt5854sup1.cif

e-68-o1379-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013372/bt5854Isup2.hkl

e-68-o1379-Isup2.hkl^{(131.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013372/bt5854Isup3.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⋯O1ⁱ	0.86	1.89	2.747 (2)	175

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Professor Orhan Büyükgüngör for his help with the data collection and acknowledge the Ondokuz Mayıs University Research Fund for financial support. The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University is greatly appreciated.

supplementary crystallographic information

Comment

In continuation to our work on the chemical and pharmacological properties of pyrimidine derivatives, we synthesized the title compound as a potential chemotherapeutic agent. The 4-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile part of the molecule is almost planar. Some pyrimidine structures have been described in the literature (Yan et al., 2011; El-Brollosy et al., 2011; Nasir et al., 2010; Tiekink 1989; Al-Deeb et al., 2012; Durkaya et al., 2011) and the bond distances of our crystal structure is comparable with these structures.

In the crystal, the molecules form centrosymmetric dimers via intermolecular N—H···O hydrogen bonds.

Experimental

To a solution of 6-(2-methylpropyl)-4-oxo-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (2.09 g, 0.01 mol) in DMF (10 ml), 1-bromo-2-methoxyethane (1.4 g, 0.01 mol) and anhydrous potassium carbonate (1.38 g, 0.01 mol) were added and the mixture was stirred at room temperature for 12 h. Water (15 ml) was then added and the mixture was stirred for further 30 min. The separated solid was filtered, washed with cold water, dried and crystallized from water to yield 1.15 g (43%) of the title compound (C₁₂H₁₇N₃O₂S) as colorless crystals. M.P.: 113–115 ^oC. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in EtOH at room temperature. ¹H NMR (DMSO-d₆, 500.13 MHz): δ 0.93 (d, 6H, CH₃, J = 7.0 Hz), 2.12–2.15 (m, 1H, CH), 2.53 (d, 2H, CH₂CH, J = 7.0 Hz), 3.27 (s, 3H, CH₃O), 3.53 (t, 2H, CH₂S, J = 6.5 Hz), 3.56 (t, 2H, OCH₂CH₂, J = 6.5 Hz), 13.55 (s, 1H, NH). ¹³C NMR (DMSO-d₆, 125.76 MHz): δ 22.55 (CH₃), 27.94 (CH), 30.19 (CH₂S), 45.30 (CH₂CH), 58.36 (CH₃O), 70.25 (OCH₂), 95.97 (C-5), 115.55 (CN), 162.05 (C-6), 166.19 (C=O), 174.50 (C-2).