4,6-Dichloro-pyrimidine-5-carbonyl chloride → 4,6-Dichloro-N-(3-methoxy-4-(oxazol-5-yl)phenyl)pyrimidine-5-carboxamide

HRID 1052454Notes

Reaction equation

HRID 1052454 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]=[CH:19][C:20]=1[C:21]1[O:25][CH:24]=[N:23][CH:22]=1)[NH2:17]>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([NH:17][C:16]2[CH:18]=[CH:19][C:20]([C:21]3[O:25][CH:24]=[N:23][CH:22]=3)=[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 121633604,6-Dichloro-pyrimidine-5-carbonyl chlorideHCID 154627323-Methoxy-4-(oxazol-5-yl)aniline

Product 1

HCID 901022024,6-Dichloro-N-(3-methoxy-4-(oxazol-5-yl)phenyl)pyrimidine-5-carboxamideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4,6-Dichloropyrimidine-5-carbonyl chloride (600 mg, 2.84 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was dissolved in dichloromethane (5 ml) and TEA (395 μl, 2.83 mmol) was added. To this solution, 3-methoxy-4-(oxazol-5-yl)aniline (540 mg, 2.84 mmol, prepared according to S. H. Watterson et al. Bio. Med. Chem. Lett. 12 (2002) 2879-2882) in 5 ml DCM was dropwise added 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 (844 mg, 87% purity, 71% yield) was used in the next synthetic step without further purification.

Workup

  1. washwashed with 4% sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude (844 mg, 87% purity, 71% yield) was used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-8213b185e4384bca94006e36d15d88ac
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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