3-Fluoro-4-methoxyaniline → 4,6-Dichloro-N-(3-fluoro-4-methoxyphenyl)pyrimidine-5-carboxamide

HRID 1052437Notes

Reaction equation

HRID 1052437 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[NH2:16]>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([NH:16][C:15]2[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:13]([F:12])[CH:14]=2)=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 5811103-Fluoro-4-methoxyanilineHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chloride

Product 1

HCID 1184337684,6-Dichloro-N-(3-fluoro-4-methoxyphenyl)pyrimidine-5-carboxamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4,6-Dichloropyrimidine-5-carbonyl chloride (890 mg, 4.21 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was dissolved in dichloromethane (3 ml) and TEA (587 μl, 4.21 mmol) was added. To this solution, 3-fluoro-4-methoxyaniline (594 mg, 4.21 mmol) dissolved in 3 ml dichloromethane was added dropwise and the mixture was stirred for 30 min. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. The crude was purified using SP1® Purification System (0%-40%, hexane-ethyl acetate) to give 720 mg (56% yield) to the title compound as an oil.

Workup

  1. additionwas added dropwise
  2. washwashed with 4% sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified
  7. customSP1® Purification System (0%-40%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b30b5dd52a3748f391ae2d37a8bb9471
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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