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 2174642Notes

Reaction equation

HRID 2174642 reaction equation
[CH3:1][C:2]1[C:7]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:11][N:10]=2)=[CH:6][C:5]([N+:21]([O-])=O)=[CH:4][N:3]=1>O.NN.CO>[CH3:1][C:2]1[C:7]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:11][N:10]=2)=[CH:6][C:5]([NH2:21])=[CH:4][N:3]=1

Participants

4

Reactant 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 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

A mixture of (2-methyl-5-nitro-pyridin-3-yl)-(4-pyridin-3-yl-pyrimidin-2-yl)-amine (450 mg, 11.84 mmol), catalytic ferric chloride (50 mg) in hydrazine hydrate (20 mL) and methanol (20 mL) was refluxed for 1 h. The reaction mixture was cooled to rt, concentrated under reduced pressure and the crude residue was diluted with water (10 mL) and extracted with EtOAc (2×25 mL). The combined extracts were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure. The residue was stirred with hexane (20 mL) for 5 min, the hexane layer was decanted and the residue was dried to give 280 mg of product as a pale yellow solid (Yield: 68%). Mp: 135° C.; 1H NMR (200 MHz, CDCl3): δ 2.51 (s, 3H), 3.65 (bs, 2H), 6.99 (s, 1H), 7.22 (d, J=4.0 Hz, 1H), 7.44 (m, 1H), 7.78 (d, J=10.0 Hz, 1H), 8.05 (d, J=2 Hz, 1H), 8.36-8.31 (m, 1H), 8.51 (d, J=4.0 Hz, 1H), 8.75-8.72 (m, 1H), 9.27 (d, J=2.0 Hz, 1H); Mass [M+H]+: 279.

Workup

  1. temperaturewas refluxed for 1 h
  2. concentrationconcentrated under reduced pressure
  3. additionthe crude residue was diluted with water (10 mL)
  4. extractionextracted with EtOAc (2×25 mL)
  5. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe hexane layer was decanted
  9. customthe residue was dried

Sources & evidence

ORD record
ord-8d6f5a5281694115922219f0cb72cf98
Source dataset
uspto-grants-2015_06
Patent number
US09062023B2

Reaction notes

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