2-Methoxyaniline → 4,6-Dichloro-N-(2-methoxyphenyl)-5-pyrimidinecarboxamide

HRID 1052460Notes

Reaction equation

HRID 1052460 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:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16]>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH3:12])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chloride

Product 1

HCID 901027264,6-Dichloro-N-(2-methoxyphenyl)-5-pyrimidinecarboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4,6-Dichloropyrimidine-5-carbonyl chloride (587 mg, 2.78 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was dissolved in dichloromethane (2.5 ml) and TEA (400 μl, 2.87 mmol) was added. To this solution, 2-methoxyaniline (340 mg, 2.76 mmol) in 3 ml DCM was added dropwise and the mixture was stirred for 30 min at room temperature. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. After evaporation of the solvent, the residue was purified by flash chromatography using SP1® Purification System (10% to 40%, hexane-ethyl acetate) to obtain 630 mg (77% yield) of the title compound.

Workup

  1. washwashed with 4% sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by flash chromatography
  7. customSP1® Purification System (10% to 40%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-00da663c55374a1da9ab9e7748a39596
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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