Cesium carbonate → 5-((4-(tert-butyldimethylsilyloxy)phenoxy)methyl)-N-(3,4-dichlorophenyl)pyrimidin-2-amine

HRID 77449ノート

反応式

HRID 77449 の反応式
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:23][C:24]1[CH:25]=[N:26][C:27]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)=[N:28][CH:29]=1>CN(C=O)C>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:23][C:24]2[CH:29]=[N:28][C:27]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=3)=[N:26][CH:25]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 5973884-(tert-Butyldimethylsiloxy)phenolHCID 866797355-(chloromethyl)-N-(3,4-dichlorophenyl)pyrimidin-2-amine

生成物 1

HCID 866797345-((4-(tert-butyldimethylsilyloxy)phenoxy)methyl)-N-(3,4-dichlorophenyl)pyrimidin-2-amine収率 12.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-((tert-butyldimethylsilyl)oxy)phenol (0.086 g, 0.381 mmol), Cs2CO3 (0.186 g, 0.572 mmol) and 5-(chloromethyl)-N-(3,4-dichlorophenyl)pyrimidin-2-amine (0.110 g, 0.381 mmol) in DMF (3.8 mL) was stirred at room temperature for 18 h. The reaction mixture was concentrated and purified by flash chromatography on silica gel using 10-50% ethyl acetate in hexanes. The desired fractions were concentrated to give 5-((4-(tert-butyldimethylsilyloxy)phenoxy)methyl)-N-(3,4-dichlorophenyl)pyrimidin-2-amine as a yellow solid (0.022 g, 12%). LCMS: R.T.=3.73 min; [M+H]+=476.23

後処理

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography on silica gel using 10-50% ethyl acetate in hexanes
  3. concentrationThe desired fractions were concentrated

出典と根拠

ORDレコード
ord-4511b193808e49c78338b00a822a2c90
出典データセット
uspto-grants-2014_09
特許番号
US08841301B2

反応ノート

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