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

HRID 577419Notes

Reaction equation

HRID 577419 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-049bc2d20f9147bfba18a025b2b298e8
Source dataset
uspto-grants-2015_05
Patent number
US09040549B2

Reaction notes

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