Propyl 3-(1,2,3,4-Tetrahydro-1,3,6-trimethyl-2,4-dioxopyrimidin-5-yl)butanoate

Jin-Cong Zhuo; Hugo Wyler

doi:10.3390/M10

and

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

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Author to whom correspondence should be addressed.

Molecules1997, 2(4), M10;https://doi.org/10.3390/M10

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

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The compound 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 (249 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: 249 mg (100 %).

IR (neat): 1728vs, 1692vs, 1640vs, 1480-1420br, 1385s, 1355vs, 1285s, 1258s, 1175vs, 1010vs, 972s, 782s, 755s.

¹H-NMR (CDCl₃): 3.98 (t, J = 6.8, 2H, CO₂CH₂Et); 3.46 (s, Me-1'); 3.33 (s, Me-3'); 3.30 (m, 1H, H-3); 3.10 (dd, J = 16.3, 8.9, 1H, H-2); 2.65 (dd, J = 16.3, 5.6, 1H, H-2); 2.36 (s, 3H, Me-6'); 1.60 (m, 2H, OCH₂CH₂Me); 1.32 (d, J = 6.8, 3H, H-4); 0.90 (t, J = 7.5, CO₂CH₂CH₂CH₃).

¹³C-NMR (CDCl₃): 173.3 (CO₂CH₂CH₂CH₃), 161.7 (C-4'), 151.9 (C-2'), 147.5 (C-6'), 113.3 (C-5'), 65.6 (CO₂CH₂CH₂CH₃), 38.5 (C-2), 32.2 (Me-3'), 30.4 (C-3), 27.7 (Me-1'), 21.8 (CO₂CH₂CH₂CH₃), 18.7 (C-4), 16.2 (Me-6'), 10.1 (CO₂CH₂CH₂CH₃).

EI-MS: 283 (M+H⁺, 4), 282 (M⁺, 4), 223 (21), 207 (13), 196 (25), 195 (50), 194 (32), 182 (51), 181 (76), 179 (17), 124 (11), 94 (6), 69 (3), 56 (100), 55 (5).

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. [CrossRef]

Sample Availability: Available from MDPI, 0.3g, MDPI 10060.

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