反应详情

A solution of 4.5 mL of oxalyl chloride in 35 mL of dichloromethane was added dropwise over 25 minutes to an ice water bath-cooled solution of 7.0 mL of N,N-diisopropylformamide in 65 mL of dichloromethane with magnetic stirring. After a few minutes, 4.74 g of 2-amino-4-hydroxy-5-iodopyrimidine was added in one portion. The bath was removed and the solution was stirred at room temperature for 30 minutes, then refluxed for one and one half hours. The solution was cooled and poured into an equal amount of ice-cold saturated aqueous sodium bicarbonate with stirring. The two phases were partitioned and the organic layer washed with additional bicarbonate(2×), water(1×) and finally saturated aqueous brine. After drying over sodium sulfate and filtration, the solution was evaporated in vacuo to yield 10.13 g of a reddish oil. The oil was purified by column chromatography on silica gel, eluting with dichloromethane. Like fractions were pooled, evaporated and triturated with hexanes to give white free flowing crystals, 5.94 g, m.p. 97–100° C.

1. waitAfter a few minutes
2. customThe bath was removed
3. temperaturerefluxed for one and one half hours
4. temperatureThe solution was cooled
5. additionpoured into an equal amount of ice-cold saturated aqueous sodium bicarbonate
6. stirringwith stirring
7. customThe two phases were partitioned
8. washthe organic layer washed with additional bicarbonate(2×), water(1×) and finally saturated aqueous brine
9. dry with materialAfter drying over sodium sulfate and filtration
10. customthe solution was evaporated in vacuo