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15 April 1997

1-Ethyl 4-propyl 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate

and
Institute of Organic Chemistry, University of Lausanne, BCH, CH-1015 Lausanne-Dorigny, Switzerland
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Molecules1997, 2(4), M6;https://doi.org/10.3390/M6
This article belongs to the Section Molbank Section of Molecules, 1997-2001
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Molecules 02 m6 i001
The diester 2 was prepared by the addition of propanol to 1 according to the reported procedure [1].
Propanol (1 ml) was added to a solution of 1 (293 mg, 1 mmol) in CH2Cl2 (5 ml). The mixture was left at r.t. for 30 min. Evaporation of the solvent under reduced pressure afforded the title compound 2, a colourless oil: 325 mg (100 %).
IR (neat): 3070m, 1730vs, 1705vs, 1660vs, 1640vs, 1480s, 1460s, 1390s, 1375s, 1345s, 1270vs, 1190vs, 1155vs, 1095s, 1020s, 780s, 755s.
1H-NMR (CDCl3): 7.23 (s, 1H, H-6'); 4.17 and 4.12 (2x dq, J = 11.0, 7.1, CO2CH2Me), 4.02 and 3.98 (dt, J = 11.0, 7.0, CO2CH2Et); 3.89 (dd, J = 7.5, 6.5, H-2); 3.37 (s, Me-1'); 3.31 (s, Me-3'); 3.05 (dd, J = 17.2, 6.5, 1H, H-3); 2.76 (dd, J = 17.2, 7.5, 1H, H-3); 1.60 (m, 2H, OCH2CH2Me); 1.21 (t, J = 7.1, CO2CH2CH3); 0.89 (t, J = 7.5, CO2CH2CH2CH3).
13C-NMR (CDCl3): 171.5 (2 COO), 162.2 (C-4'), 151.2 (C-2'), 141.5 (C-6'), 110.2 (C-5'), 66.0 (CO2CH2CH2CH3), 61.1 (CO2CH2Me), 39.8 (C-2), 36.8 (Me-3'), 35.0 (C-3), 27.7 (Me-1'), 21.6 (CO2CH2CH2CH3),13.8 (CO2CH2CH3), 10.0 (CO2CH2CH2CH3).
EI-MS: 327 (M+H+, 1), 326 (M+, 4), 281(9), 280 (23), 267 (11), 266 (7), 252 (32), 239 (7), 238 (23), 237 (17), 194 (13), 193 (100), 167 (16), 166 (26), 165 (19), 110 (26), 81 (45), 80 (25), 69 (9), 68 (15), 56 (7).

Supplementary materials

Supplementary File 1Supplementary File 2

Acknowledgments

We thank the Swiss National Foundation for financial support.

References

  1. Zhuo, J.-C.; Wyler, H. Helv. Chim. Acta 1993, 76, 1916.
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1-Ethyl 4-(2-methoxyethyl) 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate
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