Sodium Chloride → HCID 54017983, compound

Participants

Reaction Steps

A 1 liter round bottomed flask was charged with 95% sodium hydride (5.5 g, 220 mmol), dry dimethylsulfoxide (400 ml), and was cooled in an ice bath. 6-Amino-1-methyluracil (28.2 g, 200 mmol) was added slowly in portions. After evolution of hydrogen gas had subsided, the mixture was warmed to room temperature and stirred until the solid had completely dissolved (1 hour). (R)-5-Acetoxy-1-chlorohexane (37.5 g, 210 mmol), prepared as described by Klein, J. P.; Leigh, A. J.; Michnick, J.; Kumar, A. M.; Underiner, G. E. Asymmetric Synthesis of Chiral Secondary Alcohols, U.S. Pat. No. 5,629,423 (May 13, 1997), was added slowly. The mixture was heated at 80° C. for 18 hours, and after cooling to room temperature, was treated with saturated aqueous sodium chloride solution (1 L) and extracted with ethyl acetate (4×200 ml). The combined extracts were washed again with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was treated with diethyl ether (100 ml) and stirred for 18 hours. The solid was filtered, rinsed with diethyl ether, and dried under vacuum to provide (R)-3-(5-acetoxyhexyl)-6-amino-1-methyluracil (37 g, 65% yield) as a beige powder. 1H NMR (300 MHz, CDCl3) δ 1.17 (d, 3H), 1.25-1.71 (m, 6H), 2.00 (s, 3H), (t, 2H), 4.75-4.90 (m, 3H), 4.95 (s, 1H).

Provenance & Evidence