Potassium Carbonate → N-(2-Bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amine

HRID 1614968Notes

Reaction equation

HRID 1614968 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][NH2:11].[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([Cl:20])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][NH:11][C:15]1[C:16]([Cl:20])=[CH:17][N:18]=[C:13]([Cl:12])[N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 24691009(2-Bromo-5-methoxyphenyl)methanamine

Product 1

HCID 58467869N-(2-Bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amineYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-bromo-5-methoxyphenyl)methanamine (3.6 g, 13 mmol) and 2,4,5-trichloropyrimidine (1.60 mL, 14 mmol) in N,N-dimethylformamide (41.3 mL) was added potassium carbonate (5.53 g, 40 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated to give the desired product as a light yellow gel (4.65 g, 96%). LCMS for C12H10BrCl2N3O (M+H)+: m/z=361.9, 363.9.

Workup

  1. customThe reaction was quenched with water
  2. additionEtOAc was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washThe combined organic layers were washed with water and brine successively
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d3eee0baa05e42968a9067e36011ef7c
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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