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15 April 1997

1-Ethyl 4-(1-methylethyl) 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), M7;https://doi.org/10.3390/M7
This article belongs to the Section Molbank Section of Molecules, 1997-2001
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Molecules 02 m7 g001 550
Scheme.
Scheme.
Molecules 02 m7 g001
The diester 2 was prepared by the addition of iso-propanol to 1 according to the reported procedure [1].
iso-Propanol (1ml) was added to a solution of 1 (293 mg, 1mmol) in CH2Cl2 (5 ml). The mixture was left at r.t. for 1h. 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, 1370s, 1300-1140br, 1105vs, 1045s, 1020s, 960s, 935s, 925s, 860s, 780s, 755s.
1H-NMR (CDCl3): 7.24 (s, 1H, H-6'); 4.96 (hep, J = 6.5, OCHMe2); 4.20 and 4.14 (2x dq, J = 11.0, 7.1, CO2CH2Me), 3.92 (dd, J = 7.2, 6.8, H-2); 3.39 (s, Me-1'); 3.33 (s, Me-3'); 3.01 (dd, J = 17.1, 6.8, 1H, H-3); 2.73 (dd, J = 17.1, 7.2, 1H, H-3); 1.24 (t, J = 7.1, CO2CH2CH3); 1.22 (d, J = 6.5, 3H, CO2CH(CH3)2); 1.19 (d, J = 6.5, 3H, CO2CH(CH3)2).
13C-NMR (CDCl3): 171.5 (CO2CH2Me), 170.7 (CO2CH(CH3)2), 162.1 (C-4'), 151.1 (C-2'), 141.4 (C-6'), 110.1 (C-5'), 67.8 (CO2CH(CH3)2), 61.0 (CO2CH2Me), 39.6 (C-2), 36.7 (Me-3'), 35.3 (C-3), 27.6 (Me-1'), 21.4 (CO2CH(CH3)2), 13.7 (CO2CH2CH3).
EI-MS: 327 (M+H+, 2), 326 (M+, 8), 281(3), 280 (13), 267 (16), 266 (9), 252 (2), 239 (24), 238 (60), 237 (22), 210 (32), 194 (12), 193 (100), 169 (7), 167 (34), 166 (45), 165 (27), 110 (26), 81 (47), 80 (25), 69 (7), 68 (11), 56 (5).

Supplementary Materials

Supplementary File 1Supplementary File 2

Acknowledgment

We thank the Swiss National Foundation for financial support.

References

  1. Zhuo, J.-C.; Wyler, H. Helv. Chim. Acta 1993, 76, 1916. [CrossRef]
  • Sample Availability: Available from MDPI, 0.3g, MDPI 10057.

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