Dimethylformamide → 5-(2,4-Difluorophenylaminomethyl)pyrimidine

HRID 2351976Notes

Reaction equation

HRID 2351976 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1.CN(C)C=O.[F:14][C:15]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:16]=1[NH2:17].C(=O)(O)[O-].[Na+]>O.ClCCl>[F:14][C:15]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:16]=1[NH:17][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 97092,4-DifluoroanilineHCID 516892Sodium BicarbonateHCID 147202965-(Chloromethyl)pyrimidine

Product 1

HCID 147202975-(2,4-Difluorophenylaminomethyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 26.7 g. portion of 5-chloromethylpyrimidine was dissolved in 25 ml. of dimethylformamide, and 9.4 g. of 2,4-difluoroaniline was added, followed by 6.1 g. of sodium bicarbonate. The mixture was stirred for several days with gentle heating. It was then diluted with water and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and evaporated under vacuum to obtain 13.75 g. of oil. The oil was dissolved in dichloromethane and purified over silica gel, eluting with dichloromethane, to obtain 4.9 g. of the desired intermediate product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum
  5. customto obtain 13.75 g
  6. custompurified over silica gel
  7. washeluting with dichloromethane
  8. customto obtain 4.9 g

Sources & evidence

ORD record
ord-ab79d7c96d77491996b56a547c151a16
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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