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 1248317Notes

Reaction equation

HRID 1248317 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-7111d8bc662c47acba85dadff6670365
Source dataset
uspto-grants-1985_06
Patent number
US04523015

Reaction notes

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