4,6-Dichloro-pyrimidine-5-carbonyl chloride → 4,6-Dichloro-N-(3-fluoro-5-methoxyphenyl)pyrimidine-5-carboxamide

HRID 1052440Notes

Reaction equation

HRID 1052440 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]=[C:18]([O:20][CH3:21])[CH:19]=1)[NH2:16]>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([NH:16][C:15]2[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[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 121633604,6-Dichloro-pyrimidine-5-carbonyl chlorideHCID 404278903-Fluoro-5-methoxyaniline

Product 1

HCID 1184339204,6-Dichloro-N-(3-fluoro-5-methoxyphenyl)pyrimidine-5-carboxamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4,6-Dichloropyrimidine-5-carbonyl chloride (590 mg, 2.79 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was dissolved in dichloromethane (3 ml) and TEA (389 μl, 2.79 mmol) was added. To this solution, 3-fluoro-5-methoxyaniline (394 mg, 2.79 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 (800 mg, 56% purity, 51% yield) was used in the next synthetic step without further purification.

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 (800 mg, 56% purity, 51% yield) was used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-3d1081f512fd4dc7a491dfe3ad3ffd4b
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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