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Short Note

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

by
Jin-Cong Zhuo
* and
Hugo Wyler
Institute of Organic Chemistry, University of Lausanne, BCH, CH-1015 Lausanne-Dorigny, Switzerland
*
Author to whom correspondence should be addressed.
Molecules 1997, 2(4), M5; https://doi.org/10.3390/M5
Submission received: 1 February 1997 / Published: 15 April 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Browse Figure
Versions Notes
Molecules 02 m5 sch001 550
Scheme.
Scheme.
Molecules 02 m5 sch001
The diester 2 was prepared by the addition of 2-methoxyethanol to 1 according to the reported procedure [1].
2-Methoxyethanol (0.16 ml, 2 mmol) 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 and filtered through a pad of silica gel (EtOAc) afforded the title compound 2, a colourless oil: 340 mg (99 %).
IR (neat): 3070m, 1733vs, 1702vs, 1660vs, 1640vs, 1480s, 1460s, 1375s, 1345s, 1270s, 1255s, 1155s, 1128s, 1095s, 1030s, 920s, 860s, 780s, 755s.
1H-NMR (CDCl3): 7.26 (s, 1H, H-6'); 4.24 and 4.20 (2x dt, J = 12.0, 4.6, CO2CH2CH2OMe); 4.20 and 4.17 (2x dq, J = 11.0, 7.1, CO2CH2Me), 3.91 (dd, J = 7.8, 6.0, H-2); 3.58 (t, J = 4.6, CO2CH2CH2OMe); 3.40 (s, Me-1'); 3.37 (OMe); 3.34 (s, Me-3'); 3.12 (dd, J = 17.2, 6.0, 1H, H-3); 2.86 (dd, J = 17.2, 7.8, 1H, H-3); 1.24 (t, J = 7.1, CO2CH2Me).
13C-NMR (CDCl3): 171.1 (C-4), 171.0 (C-1), 161.9 (C-4'), 151.0 (C-2'), 141.6 (C-6'), 109.7 (C-5'), 69.7 (OCH2CH2OMe), 63.2 (OCH2CH2OMe), 60.8 (CO2CH2Me), 58.3 (OCH3), 39.7 (C-2), 36.5 (Me-3'), 34.7 (C-3), 27.4 (Me-1'), 13.5 (CO2CH2CH3).
EI-MS: 342 (M+, 4), 297(7), 296 (20), 268 (19), 267 (8), 266 (17), 239 (8), 238 (33), 237 (14), 194 (15), 193 (100), 167 (8), 166 (26), 165 (19), 110 (5), 81 (28), 80 (15), 69 (4), 68 (7), 59 (29), 56 (2).

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 10055.

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MDPI and ACS Style

Zhuo, J.-C.; Wyler, H. 1-Ethyl 4-(2-methoxyethyl) 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate. Molecules 1997, 2, M5. https://doi.org/10.3390/M5

AMA Style

Zhuo J-C, Wyler H. 1-Ethyl 4-(2-methoxyethyl) 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate. Molecules. 1997; 2(4):M5. https://doi.org/10.3390/M5

Chicago/Turabian Style

Zhuo, Jin-Cong, and Hugo Wyler. 1997. "1-Ethyl 4-(2-methoxyethyl) 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate" Molecules 2, no. 4: M5. https://doi.org/10.3390/M5

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