Sodium hydride → 6-Amino-2-methoxy-4-(4-acetoxybutyl)pyrimidine

HRID 1836196

반응식

HRID 1836196 반응식
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([O:10][CH3:11])[NH:7][C:6](=O)[CH:5]=1.[Br-].[Li+].[C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22]Br)(=[O:17])[CH3:16]>CN(C=O)C>[NH2:3][C:4]1[N:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6]([CH2:22][CH2:21][CH2:20][CH2:19][O:18][C:15](=[O:17])[CH3:16])[CH:5]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 82050Lithium BromideHCID 1354042146-Amino-2-methoxy-3,4-dihydropyrimidin-4-one

생성물 1

HCID 234990886-Amino-2-methoxy-4-(4-acetoxybutyl)pyrimidine수율 16%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (60% dispersion in mineral oil, 8.2 g, 205 mmol) was added to a mixture of 6-amino-2-methoxy-4-pyrimidone (24.0 g, 170 mmol) in DMF at 0° C. After 0.5 hours, lithium bromide (19.2 g, 221 mmol) was added to the mixture and stirred for 0.5 hours at room temperature. The temperature was slowly increased to 70° C., and a solution of 4-bromobutyl acetate (50 g, 256 mmol) in DMF was added dropwise to the reaction mixture. The mixture was stirred at 70° C. for 3 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was purified by chromatography on silica gel using CHCl3/MeOH (1-5%) as eluent to give first 6.5 g (15%) of 6-amino-2-methoxy-4-(4-acetoxybutyl)pyrimidine as a white solid followed by 23.4 g (yield 54%) of 6-amino-2-methoxy-3-(4-acetoxybutyl)-4-pyrimidone as a white solid.

후처리

  1. temperatureThe temperature was slowly increased to 70° C.
  2. stirringThe mixture was stirred at 70° C. for 3 hours
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-f59ba468b9db4e56939ac0bf61cb8952
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777420B2

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