N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amine → 2-Methyl-N3-(4-(pyridin-3-yl)pyriMidin-2-yl)pyridine-3,5-diaMine

HRID 1926589Notes

Reaction equation

HRID 1926589 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][N:13]=2)[C:7]([CH3:10])=[N:8][CH:9]=1)([O-])=O.[H][H]>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][N:13]=2)[C:7]([CH3:10])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 46910559N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 469098562-Methyl-N3-(4-(pyridin-3-yl)pyriMidin-2-yl)pyridine-3,5-diaMineYield 103.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of N-(5-nitro-2-methylpyrid-3-yl)-4-(pyrid-3-yl)-2-pyrimidinamine (3.0 g) in methanol (100 mL) was added activated nickel (0.3 g). Hydrogen was added to the reaction mixture at atmospheric pressure till the starting material disappeared. The solid was filtered off and the filtrate was concentrated to give the N-(5-amino-2-methylpyrid-3-yl)-4-(pyrid-3-yl)-2-pyrimidinamine (2.8 g).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3abc69afe3ab4ca8b30b40c24a30d0b0
Source dataset
uspto-grants-2012_05
Patent number
US08183242B2

Reaction notes

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