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

HRID 77449노트

반응식

HRID 77449 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-4511b193808e49c78338b00a822a2c90
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841301B2

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