4-Methoxybenzenesulfonyl chloride → 4-Amino-5-fluoro-1-(4-methoxyphenylsulfonyl)pyrimidin-2(1H)-one

HRID 631838노트

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HRID 631838 반응식
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(#N)C>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([S:18]([C:15]2[CH:14]=[CH:13][C:12]([O:11][CH3:10])=[CH:17][CH:16]=2)(=[O:20])=[O:19])[C:4](=[O:9])[N:3]=1

참가 물질

4

반응물 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 178509007HCID 178509007, 화합물

생성물 1

HCID 581384004-Amino-5-fluoro-1-(4-methoxyphenylsulfonyl)pyrimidin-2(1H)-one수율 64%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

To commercially available 4-amino-5-fluoro-pyrimidin-2-ol (1.0 grams (g), 7.75 millimoles (mmol)) in acetonitrile (CH3CN; 50 milliliters (mL)) was added bis-N, O-trimethylsilylacetamide (BSA; 5.7 mL, 23.3 mmol) and the mixture was heated at 70° C. for 1 hour (h), resulting in a clear solution. After cooling to room temperature, 4-methoxybenzene-1-sulfonyl chloride (1.8 g, 8.5 mmol) was added, and the mixture was stirred for 24 h. The solvent was evaporated and the residue was partitioned between ethyl acetate (EtOAc) and brine. The organic phase was dried over magnesium sulfate (MgSO4), filtered, and evaporated to yield the product as a pale yellow solid (1.48 g, 64%): mp 182-185° C.; 1H NMR (300 MHz, CDCl3) δ 8.40 (br s, 1H), 8.11 (d, J=5.9 Hz, 1H), 8.04-7.98 (m, 2H), 7.02-6.96 (m, 2H), 5.77 (br s, 1H), 3.88 (s, 3H); ESIMS m/z 300 ([M+H]+).

후처리

  1. customresulting in a clear solution
  2. temperatureAfter cooling to room temperature
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between ethyl acetate (EtOAc) and brine
  5. dry with materialThe organic phase was dried over magnesium sulfate (MgSO4)
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-b3da749e581c4393a4fd95432b0f4920
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321734B2

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