Dimethylformamide → 2-Chloro-N-(1-methyl-1h-benzimidazol-4-yl)-thieno[3,2-d]pyrimidine-7-carboxamide

HRID 1773618Notes

Reaction equation

HRID 1773618 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]([OH:13])=O)[C:6]=2[N:7]=1.C(N(CC)C(C)C)(C)C.[CH3:23][N:24]([CH3:27])[CH:25]=O.C1CN(C(O[N:40]2N=[N:47][C:46]3[C:41]2=C[CH:43]=[CH:44][CH:45]=3)=[N+]2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.O>[CH3:23][N:24]1[C:27]2[CH:43]=[CH:44][CH:45]=[C:46]([NH:47][C:11]([C:8]3[C:6]4[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=4[S:10][CH:9]=3)=[O:13])[C:41]=2[N:40]=[CH:25]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 13685355O-(Benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium HexafluorophosphateHCID 580563052-Chlorothieno[3,2-D]pyrimidine-7-carboxylic acid

Product 1

HCID 866896202-Chloro-N-(1-methyl-1h-benzimidazol-4-yl)-thieno[3,2-d]pyrimidine-7-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.050 g (0.233 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid, 0.0686 g (0.466 mmole) of 1-methyl-1H-benzol[d]imidazol-4-amine, 0.122 mL (0.699 mmole) of N,N-diisopropylethylamine and 1.55 mL of dimethylformamide was added 0.111 g (0.256 mmole) of O-(benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate. The mixture was stirred at room temperature for overnight. Water and dichloromethane were added. The aqueous layer was washed three times with dichloromethane. The combined organic layer was washed with aqueous sodium carbonate, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with hexanes-ethyl acetate (gradient 50:50-0:100) gave 0.042 g of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (1-methyl-1H-benzoimidazol-4-yl)-amide as a yellow solid.

Workup

  1. washThe aqueous layer was washed three times with dichloromethane
  2. washThe combined organic layer was washed with aqueous sodium carbonate, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography
  7. washeluting with hexanes-ethyl acetate (gradient 50:50-0:100)

Sources & evidence

ORD record
ord-89a4b8c1b8424214af09dede9380f797
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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