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15 April 1997

1-Ethyl 4-(1,1-dimethylethyl) 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), M8;https://doi.org/10.3390/M8
This article belongs to the Section Molbank Section of Molecules, 1997-2001
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Molecules 02 m8 sch001 550
Scheme.
Scheme.
Molecules 02 m8 sch001
The diester 2 was prepared by the addition of tert-butanol to 1 according to the reported procedure [1].
tert-Butanol (0.2 ml) was added to a solution of 1 (293 mg, 1 mmol) in CH2Cl2 (5 ml). The mixture was left at r.t. for 3 h. Evaporation of the solvent under reduced pressure afforded the title compound 2, a colourless oil: 340 mg (100 %).
IR (neat): 3070m, 1730vs, 1705vs, 1660vs, 1645vs, 1480s, 1460s, 1365s, 1345s, 1275s, 1255s, 1180s, 1150s, 1020s, 845s, 780s, 755s.
1H-NMR (CDCl3): 7.23 (s, 1H, H-6'); 4.20 and 4.15 (2x dq, J = 11.0, 7.1, CO2CH2Me), 3.90 (dd, J = 7.1, 6.7, H-2); 3.39 (s, Me-1'); 3.34 (s, Me-3'); 2.95 (dd, J = 16.8, 6.7, 1H, H-3); 2.67 (dd, J = 16.8, 7.1, 1H, H-3); 1.41 (s, 9H, CO2C(CH3)3); 1.24 (t, J = 7.1, CO2CH2CH3).
13C-NMR (CDCl3): 173.6 (CO2C(CH3)3), 171.5 (CO2CH2Me), 162.2 (C-4'), 151.1 (C-2'), 141.7 (C-6'), 110.0 (C-5'), 69.1 (CO2C(CH3)3), 61.0 (CO2CH2Me), 39.7 (C-2), 36.7 (Me-3'), 34.6 (C-3), 27.6 (Me-1'), 30.5 (CO2C(CH3)3), 13.6 (CO2CH2CH3).
EI-MS: 340 (M+, 1), 285 (4), 284 (28), 267 (17), 266 (5), 239 (21), 238 (52), 237 (4), 210 (23), 194 (11), 193 (90), 169 (8), 167 (35), 166 (49), 165 (24), 110 (10), 81 (33), 80 (18), 69 (3), 68 (8), 59 (14), 58 (12), 57 (100), 56 (11).

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.
  • Sample Availability: Available from MDPI, 0.3g, MDPI 10058.

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