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

HRID 918749ノート

反応式

HRID 918749 の反応式
[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

参加物

4

反応物 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 178509007HCID 178509007、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-63acf9d64c2e4e4199d4becd3c9df67e
出典データセット
uspto-grants-2016_03
特許番号
US09271497B2

反応ノート

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