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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 [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.093
Data-to-parameter ratio = 16.4
Details
Open access

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

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-H...O hydrogen bond with the hydroxyl functionality. In the crystal, molecules are linked into chains along the b axis by N-H...O 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[Steigbigel, R. T. et al. (2008). N. Engl. J. Med. 359, 339-354.]). For the synthesis of raltegravir, see: Belyk et al. (2006[Belyk, K. M., Morrison, H. G., Jones, P. & Summa, V. (2006). Patent No. WO 2006/06712 A2.]); For related structures, see: Fun et al. (2011[Fun, H.-K., Sumangala, V., Prasad, D. J., Poojary, B. & Chantrapromma, S. (2011). Acta Cryst. E67, o274.]); Shang, Ha, Yu & Zhao (2011[Shang, Z., Ha, J., Yu, Y. & Zhao, X. (2011). Acta Cryst. E67, o1336.]); Shang, Qi, Tao & Zhang (2011[Shang, Z., Qi, S., Tao, X. & Zhang, G. (2011). Acta Cryst. E67, o1335.]).

[Scheme 1]

Experimental

Crystal data
  • C18H21N3O6

  • Mr = 375.38

  • Monoclinic, P 21 /n

  • a = 10.540 (2) Å

  • b = 12.927 (3) Å

  • c = 13.751 (3) Å

  • [beta] = 109.74 (3)°

  • V = 1763.5 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.979, Tmax = 0.987

  • 12669 measured reflections

  • 4184 independent reflections

  • 2889 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O3 0.876 (13) 1.782 (14) 2.5879 (12) 151.9 (14)
N3-H3...O1i 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[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]).


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.  [CSD] [CrossRef] [details]
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.  [CSD] [CrossRef] [details]
Shang, Z., Qi, S., Tao, X. & Zhang, G. (2011). Acta Cryst. E67, o1335.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Steigbigel, R. T. et al. (2008). N. Engl. J. Med. 359, 339-354.  [CrossRef] [PubMed]


Acta Cryst (2012). E68, o3175  [ doi:10.1107/S160053681204233X ]

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