Pyridine → N-(4-amino-5-pyrimidinyl)-4-fluorobenzamide

HRID 2248791Notes

Reaction equation

HRID 2248791 reaction equation
[N:1]1[CH:6]=[C:5]([NH2:7])[C:4]([NH2:8])=[N:3][CH:2]=1.N1C=CC=CC=1.CN(C)C=O.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>O>[NH2:8][C:4]1[C:5]([NH:7][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([F:20])=[CH:22][CH:23]=2)=[CH:6][N:1]=[CH:2][N:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228Dimethylformamide2×HCID 678794-Fluorobenzoyl chlorideHCID 837034,5-Diaminopyrimidine

Product 1

HCID 19785297N-(4-amino-5-pyrimidinyl)-4-fluorobenzamideYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 20.2 parts of 4,5-pyrimidinediamine, 40 parts of pyridine and 144 parts of N,N-dimethylformamide was added dropwise a solution of 24.2 parts of 4-fluorobenzoyl chloride in 36 parts of N,N-dimethylformamide at 10° C. Upon completion, stirring was continued for 30 minutes at room temperature. 600 Parts of water were added. The product was filtered off and dried, yielding 30 parts (70%) of N-(4-amino-5-pyrimidinyl)-4-fluorobenzamide (interm. 11).

Workup

  1. filtrationThe product was filtered off
  2. customdried

Sources & evidence

ORD record
ord-65c0860ad69045ac88feb8773b6080cc
Source dataset
uspto-grants-1991_08
Patent number
US05041448

Reaction notes

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