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

Jin-Cong Zhuo* and Hugo Wyler

Institute of Organic Chemistry, University of Lausanne, BCH, CH-1015 Lausanne-Dorigny, Switzerland.
Fax: ++ 41 21 692 3955 ([email protected])

Received: 1 February 1997 / Published: 15 April 1997

Scheme

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).

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 10060.

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