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

HRID 1619629Notes

Reaction equation

HRID 1619629 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>C(O)C.O>[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 3

HCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 5972502,4-Dimethoxybenzylamine

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

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 a Biotage Initiator™ microwave at 120° C. for 15 minutes. The reaction mixture was diluted with water and extracted with dichloromethane (×3). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by 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. extractionextracted with dichloromethane (×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (20-50% ethyl acetate in heptane gradient elution)

Sources & evidence

ORD record
ord-f77c0f0985384a008cb35189ef6c7b14
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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