Triethylamine → 6-Chloro-N4-[(2-chlorophenyl)methyl]-2,4-pyrimidinediamine

HRID 2367243Notes

Reaction equation

HRID 2367243 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][NH2:18].C(N(CC)CC)C>CO>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:18][CH2:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[Cl:10])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidineHCID 666482-Chlorobenzylamine

Product 1

HCID 142574296-Chloro-N4-[(2-chlorophenyl)methyl]-2,4-pyrimidinediamineYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4,6-dichloro-2-pyrimidinamine (1 g, 6.1 mmol), [(2-chlorophenyl)methyl]amine (2.23 g, 15.8 mmol) and triethylamine (1.86 g, 18.4 mmol) in CH3OH (40 mL) was stirred for 4 hours at 50° C. The reaction mixture was evaporated to provide a yellow residue, which was purified by SiO2 chromatography (1:1 petroleum ether:EtOAc) to afford the title compound (1.2 g) as off-white solid. LC-MS (ES) m/z=328 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated
  2. customto provide a yellow residue, which
  3. customwas purified by SiO2 chromatography (1:1 petroleum ether:EtOAc)

Sources & evidence

ORD record
ord-b79615d0c177459e90a813d49757a831
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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