Diphenyl carbonate → HCID 58138415, 화합물

HRID 1469124노트

반응식

HRID 1469124 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.[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

참가 물질

6

반응물 3

HCID 7597Diphenyl carbonateHCID 24758Sodium hydrideHCID 58138399HCID 58138399, 화합물

생성물 1

HCID 58138415HCID 58138415, 화합물수율 24.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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]−).

후처리

  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

출처 및 근거

ORD 기록
ord-4969b0de181e4eddb3c1dd20288fbdf7
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006259B2

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