Acyclic analogs of nucleosides. Synthesis of chiral 1,5-dihydroxy-4-methyl-3-oxapent-2-yl derivatives of uracil

✍ Scribed by S. N. Mikhailov; N. B. Grishko

• Publisher: Springer US
• Year: 1988
• Tongue: English
• Weight: 348 KB
• Volume: 24
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00475574

✦ Synopsis

Pyrimido [5,4-c]quinol-4-one (II). A_: To a solution of 0.5 g (2o58 mmole) of the pyrimidone (V) in 5 ml of glacial acetic acid was added 0.3 ml of a 10% solution of dimethylamine in dry benzene, and the mixture was boiled for 4 h, evaporated, triturated with water, and the (II) (0.37 g, 74%) filtered off, mp 359-361~ (from DMF); literature value [2], mp 360-362~ B_ z. To a solution of 0.8 g (3.74 mmole) of (VI) in 8 ml of glacial acetic acid was added 0~ ml of a 10% solution of dimethylamine in dry benzene. The mixture was boiled for 4 h, evaporated to 2/3 of its volume, cooled, and the solid which separated was filtered off to give 0.55 g (75%) of (II), mp 360-361~ (from DMF).