(3-methylphenyl)methanesulfonyl Chloride → 5-(benzyloxy)-N,1-dimethyl-6-oxo-2-(m-tolylmethylsulfonamido)-1,6-dihydro-pyrimidine-4-carboxamide

HRID 1409591

反応式

HRID 1409591 の反応式
CC(C)([O-])C.[K+].[NH2:7][C:8]1[N:9]([CH3:27])[C:10](=[O:26])[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]([NH:16][CH3:17])=[O:15])[N:13]=1.[CH3:28][C:29]1[CH:30]=[C:31]([CH2:35][S:36](Cl)(=[O:38])=[O:37])[CH:32]=[CH:33][CH:34]=1>C1COCC1.CN(C=O)C.CCOC(C)=O>[CH3:17][NH:16][C:14]([C:12]1[N:13]=[C:8]([NH:7][S:36]([CH2:35][C:31]2[CH:30]=[C:29]([CH3:28])[CH:34]=[CH:33][CH:32]=2)(=[O:38])=[O:37])[N:9]([CH3:27])[C:10](=[O:26])[C:11]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:15]

参加物

7

反応物 3

HCID 2760662(3-methylphenyl)methanesulfonyl Chloride2 回HCID 23665647Potassium tert-butoxideHCID 86710289HCID 86710289、化合物

生成物 1

HCID 867102905-(benzyloxy)-N,1-dimethyl-6-oxo-2-(m-tolylmethylsulfonamido)-1,6-dihydro-pyrimidine-4-carboxamide収率 29.5%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

Potassium tert-butoxide (75.9 mg, 676 μmol) was added to a solution of 2-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide (150 mg, 520 μmol) in THF (15.0 ml) and DMF (3 ml). The resulting mixture was stirred for 10 min and then cooled with an ice-bath. To this mixture was slowly added a solution of (3-methylphenyl)methanesulfonyl chloride (140 mg, 684 μmol) in THF (1 ml). The reaction mixture was stirred at room temperature overnight. A further solution of (3-methylphenyl)methanesulfonyl chloride (140 mg, 684 μmol) in THF (1 ml) was added and then the mixture was stirred at room temperature for 48 hours. The resulting mixture was diluted with EtOAc, washed with saturated NaHCO3 aqueous solution and brine. The organic layers were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (silica gel, 0% to 2% MeOH in DCM) provided the desired product as a light yellow solid (0.070 g; 29%). LCMS: m/z=457 (MH+).

後処理

  1. temperaturecooled with an ice-bath
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. stirringthe mixture was stirred at room temperature for 48 hours
  4. washwashed with saturated NaHCO3 aqueous solution and brine
  5. dry with materialThe organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6e6c9378a7ff45c288cd8399662c0aae
出典データセット
uspto-grants-2014_12
特許番号
US08921388B2

関連ノート

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