3,5-Dimethoxyaniline → 4,6-Dichloro-N-(3,5-dimethoxyphenyl)-5-pyrimidinecarboxamide

HRID 1052445Notes

Reaction equation

HRID 1052445 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.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[NH2:17]>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([NH:17][C:16]2[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=[C:14]([O:13][CH3:12])[CH:15]=2)=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 663013,5-DimethoxyanilineHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chloride

Product 1

HCID 901035974,6-Dichloro-N-(3,5-dimethoxyphenyl)-5-pyrimidinecarboxamideYield 64%

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 (283 μl, 2.03 mmol) was added. To this solution, 3,5-dimethoxyaniline (312 mg, 2.04 mmol) dissolved in 3 ml dichloromethane was added dropwise and the mixture was stirred for 60 min. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. The crude (684 mg, 62% purity, 64% 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 (684 mg, 62% purity, 64% yield) was used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-e08fb32ee734468ba1744eb3e89b6c6d
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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