Methyl 4-(4-fluoro­phen­yl)-6-isopropyl-2-[N-methyl-N-(methylsulfonyl)amino]­pyrimidine-5-carboxyl­ate

Wei He; Dong-Ling Yang; Yong-Tao Cui; Ye-Ming Xu; Cheng Guo

doi:10.1107/S1600536808013524

. 2008 May 21;64(Pt 6):o1126. doi: 10.1107/S1600536808013524

Methyl 4-(4-fluorophenyl)-6-isopropyl-2-[N-methyl-N-(methylsulfonyl)amino]pyrimidine-5-carboxylate

Wei He ^a, Dong-Ling Yang ^b, Yong-Tao Cui ^a, Ye-Ming Xu ^a, Cheng Guo ^a,^*

PMCID: PMC2961513 PMID: 21202637

Abstract

In the molecule of the title compound, C₁₇H₂₀FN₃O₄S, the pyrimidine and benzene rings are oriented at a dihedral angle of 35.59 (3)°. Intramolecular C—H⋯N and C—H⋯O hydrogen bonds result in the formation of one five- and two six-membered non-planar rings. One of the six-membered rings adopts a chair conformation, while the other six-membered ring and the five-membered ring exhibit envelope conformations with O and N atoms displaced by 0.837 (3) and 0.152 (3) Å, respectively from the planes of the other ring atoms. In the crystal structure, intermolecular C—H⋯F hydrogen bonds link the molecules into infinite chains.

Related literature

For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₇H₂₀FN₃O₄S
M _r = 381.42
Orthorhombic,
a = 9.886 (2) Å
b = 9.988 (2) Å
c = 18.819 (4) Å
V = 1858.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 294 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.939, T _max = 0.979
3641 measured reflections
3641 independent reflections
2501 reflections with I > 2σ(I)
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.075
wR(F ²) = 0.182
S = 1.04
3641 reflections
235 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ▶), 1755 Friedel pairs
Flack parameter: 0.14 (16)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks D, I. DOI: 10.1107/S1600536808013524/hk2456sup1.cif

e-64-o1126-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013524/hk2456Isup2.hkl

e-64-o1126-Isup2.hkl^{(178.5KB, 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
C3—H3B⋯O1	0.98	2.52	3.181 (8)	125
C10—H10B⋯N1	0.96	2.56	3.148 (7)	120
C11—H11A⋯N2	0.96	2.23	2.697 (7)	109
C11—H11C⋯Fⁱ	0.96	2.34	3.302 (8)	177

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Some derivatives of pyrimidine are important chemical materials. We report herein the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), rings A (N1/N2/C4-C7) and B (C12-C17) are, of course, planar, and the dihedral angle between them is A/B = 35.59 (3)°. The intramolecular C-H···N and C-H···O hydrogen bonds (Table 1) result in the formation of one five- and two six-membered non-planar rings: C (N2/N3/C5/C11/H11A), D (S/N1/N3/C5/C10/H10B) and E (O1/C3/C4/C7/C8/H3B), respectively. Ring D adopts chair [φ = -40.04 (2)° and θ = 134.72 (3)°] conformation, having total puckering amplitude, Q_T, of 1.188 (3) Å (Cremer & Pople, 1975). Rings C and E have envelope conformations with nitrogen and oxygen atoms displaced by 0.152 (3) Å and 0.837 (3) Å from the planes of the other ring atoms, respectively.

In the crystal structure, intermolecular C-H···F hydrogen bonds (Table 1) link the molecules into infinite chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, sodium salt of N-methyl methane sulphonamide (106 g, 631.00 mmol) and methyl 4-(4-fluorophenyl)-6-isopropyl- 2-methyl sulfonylpyrimidine-5-carboxylate (100 g, 284.06 mmol) were added to DMF (1000 ml) in a round bottom flask, and then stirred for 1 h at 303 K. After completion of the reaction, demineralized water (1000 ml) was added and stirred for 1 h. The mixture was filtered, washed with water, and then dried (yield; 95%). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.