Water → N-[(2,4-dimethoxyphenyl)methyl]pyrimidin-2-amine

HRID 509121Notes

Reaction equation

HRID 509121 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][O:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[CH2:12][NH2:13].C(N(CC)CC)C.O>C(O)C>[CH3:8][O:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[CH2:12][NH:13][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 55026262N-[(2,4-dimethoxyphenyl)methyl]pyrimidin-2-amineYield 72.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloropyrimidine (1.37 g, 12 mmol), 2,4-dimethoxybenzylamine (2.61 g, 15.6 mmol) and triethylamine (2.51 mL, 18 mmol) in ethanol (8 mL) was heated in the microwave at 120° C. for 15 minutes. Water was added to the reaction mixture and the mixture extracted with dichloromethane (×3). The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography (20-50% ethyl acetate in heptane gradient elution) to afford the title compound as a white solid (2.14 g, 72%).

Workup

  1. extractionthe mixture extracted with dichloromethane (×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washsilica gel column chromatography (20-50% ethyl acetate in heptane gradient elution)

Sources & evidence

ORD record
ord-748b085a60a94878a6567eca6e3f4311
Source dataset
uspto-grants-2015_08
Patent number
US09096558B2

Reaction notes

Loading…