2-Amino-4-chloro-6-methylpyrimidine → 4-Methyl-6-(3-methylphenyl)-2-pyrimidinamine

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1>>[CH3:9][C:4]1[CH:5]=[C:6]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:10])[CH:16]=2)[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

Reactant 2

HCID 218102-Amino-4-chloro-6-methylpyrimidine

HCID 27339503-Tolylboronic acid

Product 1

HCID 585135554-Methyl-6-(3-methylphenyl)-2-pyrimidinamine

Procedure

The title compound is synthesized according to general procedure GP4 starting from 2.0 g (14 mmol) 2-amino-4-chloro-6-methylpyrimidine and 2.5 g (18 mmol) 3-methyl-phenyl boronic acid. Yield after extraction and re-crystallization from diethylether: 4.1 g (>100%, approximately 70% pure).

Workup

customYield
extractionafter extraction and re-crystallization from diethylether

Sources & evidence

ORD record: ord-8c673d2a4f184d7385067374ab706f2d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916548B2

Reaction notes

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