Potassium Carbonate → N-(3-Bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amine

HRID 1614974Notes

Reaction equation

HRID 1614974 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][NH2:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[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:3]=[C:4]([CH:5]=[C:6]([O:8][CH3:9])[CH:7]=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 534144413-Bromo-5-methoxybenzenemethanamine

Product 1

HCID 58467901N-(3-Bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-bromo-5-methoxyphenyl)methanamine (2.57 g, 11.9 mmol) and 2,4,5-trichloropyrimidine (2.4 g, 13 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (3.3 g, 24 mmol). The resultant mixture was stirred overnight at room temperature. The reaction mixture 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. The residue was purified by silica gel column chromatography to give the desired product (3.7 g, 87%). LCMS for C12H10BrCl2N3O (M+H)+: m/z=361.9, 363.9.

Workup

  1. customThe reaction mixture 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
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7aa0bc8e71ef4a94ba0020ac5fcddb3f
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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