Potassium Carbonate → 2,5-Dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

HRID 1614927Notes

Reaction equation

HRID 1614927 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([Cl:19])=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:11][C:12]1[N:17]=[C:16]([NH:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:15]([Cl:19])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 211563-MethoxybenzylamineHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 584678982,5-Dichloro-N-(3-methoxybenzyl)pyrimidin-4-amineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methoxybenzylamine (0.75 g, 5.4 mmol) and 2,4,5-trichloropyrimidine (1.1 g, 6.0 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (2.3 g, 16 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with water. Ethyl acetate (“EtOAc”) was added and the layers were separated. The aqueous layer was extracted with EtOAc once. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated. The crude product was purified by silica gel column chromatography to give the desired product as a white powder (1.43 g, 92%). LCMS for C12H12ClN3O (M+H)+: m/z=284.0, 286.0.

Workup

  1. customThe reaction was quenched with water
  2. additionEthyl acetate (“EtOAc”) was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc once
  5. washThe combined organic layers were washed with water and brine successively
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c50a497f18a442f981a6911f87a3133f
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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