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

Jin-Cong Zhuo; Hugo Wyler

doi:10.3390/M5

and

Institute of Organic Chemistry, University of Lausanne, BCH, CH-1015 Lausanne-Dorigny, Switzerland

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Molecules1997, 2(4), M5;https://doi.org/10.3390/M5

This article belongs to the Section Molbank Section of Molecules, 1997-2001

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Scheme.

The diester 2 was prepared by the addition of 2-methoxyethanol to 1 according to the reported procedure [].

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

Zhuo, J.-C.; Wyler, H. Helv. Chim. Acta 1993, 76, 1916.

Sample Availability: Available from MDPI, 0.3g, MDPI 10055.

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