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

HRID 77449

Reaction equation

HRID 77449 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-4511b193808e49c78338b00a822a2c90
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Linked notes

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