Cesium carbonate → 2-(1-(3-(2-(4-Morpholinophenylamino)pyrimidin-4-ylthio)benzyl)-1H-imidazol-4-yl)acetonitrile

HRID 81730Notes

Reaction equation

HRID 81730 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([S:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1.[C:29]([CH2:31][C:32]1[N:33]=[CH:34][NH:35][CH:36]=1)#[N:30].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[O:26]1[CH2:27][CH2:28][N:23]([C:20]2[CH:21]=[CH:22][C:17]([NH:16][C:12]3[N:11]=[C:10]([S:9][C:5]4[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=4)[CH2:2][N:35]4[CH:36]=[C:32]([CH2:31][C:29]#[N:30])[N:33]=[CH:34]4)[CH:15]=[CH:14][N:13]=3)=[CH:18][CH:19]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 594917074-(3-(Bromomethyl)phenylthio)-N-(4-morpholinophenyl)pyrimidin-2-amineHCID 178510863HCID 178510863, compound

Product 1

HCID 594914482-(1-(3-(2-(4-Morpholinophenylamino)pyrimidin-4-ylthio)benzyl)-1H-imidazol-4-yl)acetonitrileYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-(3-(bromomethyl)phenylthio)-N-(4-morpholinophenyl)pyrimidin-2-amine (100 mg, 0.22 mmol) and 4-cyanomethyl imidazole (47 mg, 0.44 mmol) in dimethyl formamide (2 mL), was added cesium carbonate (154 mg, 0.44 mmol) in one portion. The mixture was stirred at room temperature for 16 hours. It was filtered to remove any inorganic material, and the dimethyl formamide solution was concentrated in vacuo. The residue was column chromatographed on the silica gel using methanol:dichloromethane (4:96) as eluant to give the product (50 mg, 47%).

Workup

  1. filtrationIt was filtered
  2. customto remove any inorganic material
  3. concentrationthe dimethyl formamide solution was concentrated in vacuo
  4. customchromatographed on the silica gel

Sources & evidence

ORD record
ord-da557bd64a7e4ba493a12453796b8043
Source dataset
uspto-grants-2014_09
Patent number
US08846704B2

Reaction notes

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