2-Methyl-5-Nitroaniline → 2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

HRID 1786720Notes

Reaction equation

HRID 1786720 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[CH3:24]>>[CH3:24][C:16]1[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=1[NH:14][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 74442-Methyl-5-NitroanilineHCID 118055432-Chloro-4-(pyridin-3-yl)pyrimidine

Product 1

HCID 106861492-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

Procedure

Thus, Imatinib or an addition salt thereof is obtained by a synthetic route comprising reacting 2-chloro-4-(3-pyridyl)-pyrimidine with 2-amino-4-nitro-toluene to obtain N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine, which is subsequently reduced and reacted with 4-(4-methyl-piperazine-1-ylmethyl)-benzoyl chloride to yield the final product

Sources & evidence

ORD record
ord-b227e15041494e41aa620cd9dbef7f8b
Source dataset
uspto-grants-2009_03
Patent number
US07507821B2

Reaction notes

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