Potassium Carbonate → 2,5-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amine

HRID 1614945Notes

Reaction equation

HRID 1614945 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[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>[Cl:12][C:13]1[N:18]=[C:17]([NH:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:16]([Cl:20])=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 748663-MethoxyphenethylamineHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 584678672,5-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amineYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methoxyphenethylamine (1.93 mL, 13.2 mmol) and 2,4,5-trichloropyrimidine (1.59 mL, 13.9 mmol) in N,N-dimethylformamide (40 mL) was added potassium carbonate (5.5 g, 40 mmol). The resultant 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 yellow gel (3.74 g, 95%). LCMS for C13H14Cl2N3O (M+H)+: m/z=298.0, 300.0.

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-1af3814c846d43a3bc2e857f607f7351
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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