N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramide → 2-[2-(3,4-Dimethoxy-2-pyridylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone

HRID 903371Notes

Reaction equation

HRID 903371 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+](N[C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:22][N:21]=1)([O-])=O>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH2:11][S:12][CH2:13][CH2:14][NH:15][C:20]2[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:22][N:21]=2)=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 12788688N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramideHCID 202792822-(3,4-Dimethoxy-2-pyridylmethylthio)ethylamine

Product 1

HCID 202792852-[2-(3,4-Dimethoxy-2-pyridylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-(3,4-dimethoxy-2-pyridylmethylthio)ethylamine (0.95 g, 4.16 mmol), 2-nitroamino-5-(3-pyridylmethyl)-4-pyrimidone (0.925 g, 3.74 mmol) and pyridine (3.5 ml) was heated under reflux for 24 hours and evaporated to dryness. The residue was purified by elution from silica gel with methanolchloroform (1:7) and recrystallisation from ethanol to give 2-[2-(3,4-dimethoxy-2-pyridylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone 121°-1.5°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customevaporated to dryness
  4. customThe residue was purified by elution from silica gel with methanolchloroform (1:7) and recrystallisation from ethanol

Sources & evidence

ORD record
ord-a2d96f990af64fe397c05d9c8b76a9b6
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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