Methyl iodide → N-(3-(2-chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine-6-yl)phenyl)-N-methylacetamide

HRID 2262241Notes

Reaction equation

HRID 2262241 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:15]=[CH:16][CH:17]=3)([I:11])[CH2:8][C:6]=2[N:7]=1.[C:28](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([C:12]3[CH:13]=[C:14]([N:18]([CH3:28])[C:19](=[O:21])[CH3:20])[CH:15]=[CH:16][CH:17]=3)([I:11])[CH2:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86618443HCID 86618443, compound

Product 1

HCID 86618444N-(3-(2-chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine-6-yl)phenyl)-N-methylacetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 60 mg of N-(3-(2-chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine-6-yl)phenyl)acetamide and 78 mg of cesium carbonate in DMF was added 12 μL of iodomethane. The reaction mixture was stirred for 2 h at room temperature. The mixture was diluted with ethyl acetate, washed with H2O. The organic layer was dried over (MgSO4) and evaporated to yield N-(3-(2-chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine-6-yl)phenyl)-N-methylacetamide.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried over (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-9ec528f80d764d9f8e07d0797b98e351
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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