Ethyl 6-[4-(dimethyl­amino)phen­yl]-4-hydr­oxy-2-oxo-4-(trifluoro­methyl)­hexa­hydro­pyrimidine-5-carboxyl­ate

Song, X.-P.; Li, G.-C.; Wu, C.-Z.; Yang, F.-L.

doi:10.1107/S1600536810013127

Volume 66
Part 5
Page o1083
May 2010

Received 2 April 2010
Accepted 9 April 2010
Online 14 April 2010

Key indicators
Single-crystal X-ray study
T = 116 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.107
Data-to-parameter ratio = 12.3
Details

Ethyl 6-[4-(dimethylamino)phenyl]-4-hydroxy-2-oxo-4-(trifluoromethyl)hexahydropyrimidine-5-carboxylate

Xiao-Ping Song,^a Gong-Chun Li,^a Chang-Zeng Wu ^a and Feng-Ling Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Henan Province 461000, People's Republic of China
Correspondence e-mail: actaeli@gmail.com

The title compound, C₁₆H₂₀F₃N₃O₄, was prepared by reaction of 4-(dimethylamino)benzaldehyde, ethyl 4,4,4-trifluoro-3-oxobutanoate and urea. In the title molecule, the pyrimidine ring adopts a half-chair conformation and there is an intramolecular hydrogen bond (O-HO). The crystal structure is stabilized by two types intermolecular hydrogen bonds (N-HO and N-HN).

Related literature

For the bioactivity of dihydropyrimidines, see: Brier et al. (2004); Cochran et al. (2005); Moran et al. (2007); Zorkun et al. (2006). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003); Ulrich (2004).

Experimental

Crystal data

C₁₆H₂₀F₃N₃O₄
M_r = 375.35
Monoclinic, P 2₁ /n
a = 13.319 (4) Å
b = 7.923 (2) Å
c = 16.530 (5) Å
= 92.720 (5)°
V = 1742.3 (9) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 116 K
0.24 × 0.20 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.971, T_max = 0.983
11487 measured reflections
3081 independent reflections
2522 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.107
S = 1.07
3081 reflections
250 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.17 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O3	0.86 (1)	1.97 (1)	2.7601 (16)	153 (2)
N1-H1AO2ⁱ	0.90 (1)	1.91 (1)	2.8049 (15)	174 (2)
N2-H2AN3ⁱⁱ	0.90 (1)	2.12 (1)	3.0241 (18)	178 (2)
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: OM2331 ).

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province, China (grant No. 082300420110), and the Natural Science Foundation of Henan Province Education Department, China (grant No. 2007150036).

References

Brier, S., Lemaire, D., DeBonis, S., Forest, E. & Kozielski, F. (2004). Biochemistry, 43, 13072-13082.
Cochran, J. C., Gatial, J. E., Kapoor, T. M. & Gilbert, S. P. (2005). J. Biol. Chem. 280, 12658-12667.
Hermann, B., Erwin, H. & Hansjorg, K. (2003). US Patent No. 2003176284.
Moran, M. M., Fanger, C., Chong, J. A., McNamara, C., Zhen, X. G. & &Mandel-Brehm, J. (2007). WO Patent No. 2007073505.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Ulrich, H. (2004). US Patent No. 2004033897.
Zorkun, I. S., Sarac, S., Celebi, S. & Erol, K. (2006). Bioorg. Med. Chem. 14, 8582-8589.

organic compounds