3-Methoxybenzylamine → 4,6-Dichloro-N-(3-methoxybenzyl)pyrimidine-5-carboxamide

HRID 1052457Notes

Reaction equation

HRID 1052457 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]([CH2:20][NH2:21])[CH:17]=[CH:18][CH:19]=1>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([NH:21][CH2:20][C:16]2[CH:17]=[CH:18][CH:19]=[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 211563-MethoxybenzylamineHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chloride

Product 1

HCID 901029744,6-Dichloro-N-(3-methoxybenzyl)pyrimidine-5-carboxamideYield 62%

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, (3-methoxyphenyl)methanamine (379 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 30%, hexane-ethyl acetate) to obtain 534 mg (61% 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 30%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5a52fe91af11451c85d1095e62bca43e
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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