p-Toluidine → 6-Chloro-n4-(4-methylphenyl)pyrimidine-2,4-diamine

HRID 28527

Reaction equation

HRID 28527 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1.C(N(CC)C(C)C)(C)C>C(O)C>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([CH3:10])=[CH:12][CH:13]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 655222-Amino-4,6-dichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 2387486-Chloro-n4-(4-methylphenyl)pyrimidine-2,4-diamineYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,6-dichloro-pyrimidin-2-yl-amine (3.3 g, 20 mmol), p-tolylamine (3.4 g, 32 mmol) and N,N-diisopropylethylamine (12 ml) in ethanol (150 ml) was heated under reflux for 40 hours. After cooling to room temperature, filtration provided 6-chloro-N*4*-p-tolyl-pyrimidine-2,4-diamine (2.8 g, 60% yield) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 hours
  3. filtrationfiltration

Sources & evidence

ORD record
ord-4b58f671d02747c482395d81bde4e44d
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

Loading…