N-[2-Chloro-6-(4-chloro-6-methoxy­pyrimidin-2-ylsulfan­yl)benz­yl]-3,4-dimethyl­aniline

Weijun Fu; Mei Zhu; Dongfeng Hong

doi:10.1107/S1600536809041026

. 2009 Oct 17;65(Pt 11):o2758. doi: 10.1107/S1600536809041026

N-[2-Chloro-6-(4-chloro-6-methoxypyrimidin-2-ylsulfanyl)benzyl]-3,4-dimethylaniline

Weijun Fu ^a,^*, Mei Zhu ^a, Dongfeng Hong ^a

PMCID: PMC2971454 PMID: 21578352

Abstract

In the title molecule, C₂₀H₁₉Cl₂N₃OS, the dihedral angle between the two benzene rings is 79.3 (7)°. The 4-chloro-6-methoxypyrimidine group is rotationally disordered over two sites by approximately 180°, the ratio of the refined occupancies being 0.6772 (15):0.3228 (15). Both disorder components of disorder are involved in intramolecular N—H⋯N hydrogen bonds.

Related literature

For the biological functions of pyrimidine derivatives, see: Joffe et al. (1989 ▶); Petersen & Schmidt (2003 ▶); Blum (2001 ▶); Gompper et al. (2004 ▶); Michael (2005 ▶); Nadal & Olavarria (2004 ▶).

Experimental

Crystal data

C₂₀H₁₉Cl₂N₃OS
M _r = 420.34
Monoclinic,
a = 12.3653 (12) Å
b = 14.1332 (14) Å
c = 11.8276 (11) Å
β = 97.340 (1)°
V = 2050.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 296 K
0.37 × 0.28 × 0.25 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.856, T _max = 0.899
15364 measured reflections
3804 independent reflections
2727 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.139
S = 1.04
3804 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809041026/lh2926sup1.cif

e-65-o2758-sup1.cif^{(24.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041026/lh2926Isup2.hkl

e-65-o2758-Isup2.hkl^{(186.5KB, hkl)}

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⋯N3′	0.87	2.31	3.089 (3)	150
N1—H1⋯N2	0.87	2.45	3.203 (4)	145

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Acknowledgments

This work was supported by the Doctoral Foundation of Luoyang Normal University.

supplementary crystallographic information

Comment

Pyrimidine derivatives are widespread in medicinal and natural product chemistry. A number of natural products, pharmaceuticals, and functional materials incorporate this heterocycle (Michael, 2005). Several examples of pharmaceutically important compounds include trimethoprim (Joffe et al., 1989), sulfadiazine (Petersen & Schmidt, 2003),Gleevec (imatinib mesilate) (Nadal & Olavarria, 2004), and Xeloda (capecitabine) (Blum, 2001). Natural and unnatural polymers also contain pyrimidine derivatives (Gompper et al., 2004). The potent physiological properties of these pyrimidine derivatives has led to their vast use as medicines in the field of pharmaceutical chemistry. In this context, we report the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. The bond lengths and angles are as expected. The the dihedral angle between the two benzene rings is 79.3 (7)°. The 4-chloro-6-methoxypyrimidine group is rotationlly disordered over two sites by approximately 180° with the ratio of the refined occupancies being 0.6772 (15):0.3228 (15). Both the major and minor components of disorder are involved in intramolecular N-H···N hydrogen bonds.

Experimental

To a solution of 2,4-dichloro-6-methoxypyrimidine (0.5 mmol) and 2-((3,4-dimethylphenylamino)methyl)-3-chlorobenzenethiol (0.5 mmol) in dry methylbenzene NaH (0.6 mmol) was added. The mixture was stirred for 12 h at room temperature. After evaporation of the solvent, the residue was purified by column chromatography on silica gel to afford the title compound as a colorless solid (yield 90%). The title compound was recrystallized from CH₂Cl₂ at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.