4,6-Dichloropyrimidine → 6-Chloro-N-(4-methoxybenzyl)pyrimidin-4-amine

HRID 1670200Notes

Reaction equation

HRID 1670200 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C>CCCCO>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:16][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 754524-MethoxybenzylamineHCID 81531Diisopropylethylamine

Product 1

HCID 223094976-Chloro-N-(4-methoxybenzyl)pyrimidin-4-amineYield 91.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4,6-dichloropyrimidine (Aldrich, 3.6 g, 24.2 mmol), 4-methoxybenzylamine (2.7 g, 19.7 mmol), DIPEA (5 ml, 28.8 mmol), and n-BuOH was heated at reflux for 3 h. The mixture was concentrated and the residue treated with H2O (150 mL) and EtOAc (175 mL). The EtOAc phase was separated, washed with saturated aq. NaHCO3 solution and brine, dried (MgSO4), and concentrated to give the title compound (4.5 g) which was used without further purification. 1H NMR (DMSO-d6) δ 8.29 (s, 1H), 8.13 (br s, 1H), 7.25 (d, 2H, J=8.2 Hz), 6.90 (d, 2H, J=8.2 Hz), 6.56 (s, 1H), 4.48 (s, 2H), 3.75 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationThe mixture was concentrated
  4. additionthe residue treated with H2O (150 mL) and EtOAc (175 mL)
  5. customThe EtOAc phase was separated
  6. washwashed with saturated aq. NaHCO3 solution and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c9f511c726e84762a8da465178fa87c3
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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