Oxalyl chloride → 4-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

HRID 1271027

반응식

HRID 1271027 반응식
C(Cl)(=O)C([Cl:4])=O.[CH:7]([N:10]([CH:13]([CH3:15])[CH3:14])[CH:11]=O)([CH3:9])[CH3:8].[NH2:16][C:17]1[N:22]=[C:21](O)[C:20]([I:24])=[CH:19][N:18]=1>ClCCl>[Cl:4][C:21]1[C:20]([I:24])=[CH:19][N:18]=[C:17]([N:16]=[CH:11][N:10]([CH:13]([CH3:15])[CH3:14])[CH:7]([CH3:9])[CH3:8])[N:22]=1

참가 물질

5

반응물 3

HCID 65578Oxalyl chlorideHCID 75912N,N-bis(1-methylethyl)formamideHCID 178508432HCID 178508432, 화합물

생성물 1

HCID 734464514-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2f63d07cd13644f8b01ad385cdc396fe
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205297B2

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