Methyl iodide → HCID 53474701, 화합물

HRID 2382925노트

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HRID 2382925 반응식
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:4](=[O:18])[N:3]=1.[C:19](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[C:12]1([S:9]([N:5]2[CH:6]=[C:7]([F:8])[C:2](=[NH:1])[N:3]([CH3:19])[C:4]2=[O:18])(=[O:10])=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58138399HCID 58138399, 화합물

생성물 1

HCID 53474701HCID 53474701, 화합물수율 50.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

4-Amino-1-benzenesulfonyl-5-fluoro-1H-pyrimidine-2-one (200 mg, 0.74 mmol) was stirred at room temperature in dimethyl formamide (3 mL) together with anhydrous potassium carbonate (210 mg, 1.5 mmol). Iodomethane (210 mg, 1.5 mmol) was added and the mixture was heated at 60° C. for 3 hours. After cooling to room temperature, the mixture was partitioned between ethyl acetate (EtOAc) and water. The organic phase was dried over magnesium sulfate, filtered, and evaporated. The crude product was purified by chromatography on silica gel (gradient, 20 to 80% EtOAc in petroleum ether) to isolate 1-benzenesulfonyl-5-fluoro-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one (106 mg, 50%) as a white solid: mp 144° C.; 1H NMR (600 MHz, DMSO-d6) δ 8.52 (s, 1H), 8.03-8.00 (m, 2H), 7.97 (d, J=5.9 Hz, 1H), 7.80-7.76 (m, 1H), 7.67-7.63 (m, 2H), 3.09 (s, 3H); ESIMS m/z 284 ([M+H]+).

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between ethyl acetate (EtOAc) and water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by chromatography on silica gel (gradient, 20 to 80% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-47e0a0d27b5548e791fa5cd1b2c98c7c
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263603B2

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