Diphenyl carbonate → HCID 58138415、化合物

HRID 1469124ノート

反応式

HRID 1469124 の反応式
[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.[H-].[Na+].[C:21](=O)([O:29]C1C=CC=CC=1)[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1.CCOC(C)=O>[C:23]1([O:22][C:21](=[O:29])[NH:1][C:2]2[C:7]([F:8])=[CH:6][N:5]([S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:10])=[O:11])[C:4](=[O:18])[N:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 7597Diphenyl carbonateHCID 24758Sodium hydrideHCID 58138399HCID 58138399、化合物

生成物 1

HCID 58138415HCID 58138415、化合物収率 24.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 4-amino-1-benzenesulfonyl-5-fluoro-1H-pyrimidin-2-one (0.20 g, 0.74 mmol) in anhydrous THF (3 mL) was added NaH (0.044 g of 60 wt % suspension in mineral oil, 1.11 mmol) at 0° C. After gas evolution had subsided, the mixture was transferred via cannula to an ice-cold mixture of diphenyl carbonate (1.5 g, 7.4 mmol) in anhydrous THF (5 mL) and stirred for 6 h. The reaction was diluted with EtOAc (25 mL) and the resulting solution was washed with satd aq NH4Cl (15 mL) and brine (15 mL). The organic phase was dried over Na2SO4, filtered, and the solvent evaporated. The residue was purified by precipitation from MeOH and Et2O to give (1-benzenesulfonyl-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamic acid phenyl ester as a light brown solid (0.070 g, 24%): mp 182-185° C.; 1H NMR (400 MHz, DMSO-d6) δ 7.95 (m, 2H), 7.87 (d, J=7.0 Hz, 1H), 7.71 (d, J=7.5 Hz, 1H), 7.61 (t, J=7.7 Hz, 2H), 7.33 (t, J=7.9 Hz, 2H), 7.15 (d, J=7.3 Hz, 1H), 7.06 (d, J=7.6 Hz, 2H); ESIMS m/z 390 ([M+H]+), 388 ([M−H]−).

後処理

  1. washthe resulting solution was washed with satd aq NH4Cl (15 mL) and brine (15 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue was purified by precipitation from MeOH and Et2O

出典と根拠

ORDレコード
ord-4969b0de181e4eddb3c1dd20288fbdf7
出典データセット
uspto-grants-2015_04
特許番号
US09006259B2

反応ノート

読み込み中…