Hydrazine hydrate (1:1) → 2-Methyl-N3-(4-(pyridin-3-yl)pyriMidin-2-yl)pyridine-3,5-diaMine

HRID 1926590Notes

Reaction equation

HRID 1926590 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.O.NN>C(O)C.[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 24654Hydrazine hydrate (1:1)HCID 46910559N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amine

Product 1

HCID 469098562-Methyl-N3-(4-(pyridin-3-yl)pyriMidin-2-yl)pyridine-3,5-diaMineYield 92.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of N-(5-nitro-2-methylpyrid-3-yl)-4-(pyrid-3-yl)-2-pyrimidinamine (18.0 g) and hydrazine hydrate (9 mL) in ethanol (180 mL) was added activated nickel (0. g). The mixture was refluxed for 3 hours, filtrated and the filtrate was concentrated in vacuo to give solid, which was put in the fridge (0° C.) overnight. The residue was filtrated off and the filtrate was concentrated in vacuo to give N-(5-amino-2-methylpyrid-3-yl)-4-(pyrid-3-yl)-2-pyrimidinamine (15 g).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationfiltrated
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give solid, which
  5. customwas put in the fridge (0° C.) overnight
  6. filtrationThe residue was filtrated off
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cdd6e21cdc5f46c6bcef83a5f0842c67
Source dataset
uspto-grants-2012_05
Patent number
US08183242B2

Reaction notes

Loading…