Methyl 2-[2-(benzyl­oxycarbon­ylamino)­propan-2-yl]-5-hy­droxy-1-methyl-6-oxo-1,6-dihydro­pyrimidine-4-carboxyl­ate

Shang, Z.; Tao, X.; Ha, J.; Yu, F.

doi:10.1107/S160053681204233X

Volume 68
Part 11
Page o3175
November 2012

Received 23 August 2012
Accepted 9 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.093
Data-to-parameter ratio = 16.4
Details

Methyl 2-[2-(benzyloxycarbonylamino)propan-2-yl]-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Zhenhua Shang,^a ^* Xiao Tao,^b Jing Ha ^c and Fuda Yu ^d

^aCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Hebei Research Center of Pharmaceutical and Chemical Engineering, State Key Laboratory Breeding Base-Hebei Province, Key Laboratory of Molecular Chemistry for Drugs, Shijiazhuang 050018, People's Republic of China,^bCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China,^cZhongqi Pharmacy (Shijiazhang), Shijiazhuang Pharmaceutical Group Co., Ltd (CSPC), Shijiazhuang 050051, People's Republic of China, and ^dDepartment of Neurosurgery, Shijiazhuang Center Hospital, Shijiazhuang 050011, People's Republic of China
Correspondence e-mail: zhenhuashang@yahoo.com.cn

The title pyrimidine derivative, C₁₈H₂₁N₃O₆, was obtained by the reaction of methyl 2-[2-(benzyloxycarbonyl)aminopropan-2-yl]-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate with dimethyl sulfate in dimethyl sulfoxide. The molecule has a V-shaped structure, the phenyl and the pyrimidine rings making a dihedral angle of 43.1 (1)°. The methyl group substituting the pyrimidine ring deviates slightly from the ring mean-plane [C-N-C-C torsion angle = 5.49 (15)°], and the methyl ester substituent has a conformation suitable for the formation of an intramolecular O-HO hydrogen bond with the hydroxyl functionality. In the crystal, molecules are linked into chains along the b axis by N-HO hydrogen bonds.

Related literature

For the antiretroviral drug raltegravir [systematic name: N-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)], see: Steigbigel et al. (2008). For the synthesis of raltegravir, see: Belyk et al. (2006); For related structures, see: Fun et al. (2011); Shang, Ha, Yu & Zhao (2011); Shang, Qi, Tao & Zhang (2011).

Experimental

Crystal data

C₁₈H₂₁N₃O₆
M_r = 375.38
Monoclinic, P 2₁ /n
a = 10.540 (2) Å
b = 12.927 (3) Å
c = 13.751 (3) Å
= 109.74 (3)°
V = 1763.5 (6) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.979, T_max = 0.987
12669 measured reflections
4184 independent reflections
2889 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.093
S = 1.00
4184 reflections
255 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O3	0.876 (13)	1.782 (14)	2.5879 (12)	151.9 (14)
N3-H3O1ⁱ	0.875 (15)	2.118 (15)	2.9854 (16)	170.9 (12)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2453 ).

Acknowledgements

The project was supported by the Hebei Provincial Natural Science Foundation of the China-Shijiazhuang Pharmaceutical Group (CSPC) Foundation (H2012208045), the Scientific and Technological Major Special Project (Major Creation of New Drugs, No. 2011ZX09202-101-22) and the Program for Innovative Research Team of Hebei University of Science and Technology.

References

Belyk, K. M., Morrison, H. G., Jones, P. & Summa, V. (2006). Patent No. WO 2006/06712 A2.
Fun, H.-K., Sumangala, V., Prasad, D. J., Poojary, B. & Chantrapromma, S. (2011). Acta Cryst. E67, o274.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Shang, Z., Ha, J., Yu, Y. & Zhao, X. (2011). Acta Cryst. E67, o1336.
Shang, Z., Qi, S., Tao, X. & Zhang, G. (2011). Acta Cryst. E67, o1335.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Steigbigel, R. T. et al. (2008). N. Engl. J. Med. 359, 339-354.

organic compounds