5-(5,6-Dimethyl-3-pyridylmethyl)-2-nitroamino4-pyrimidone → 2-[2-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamino]-5-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidone

HRID 851493Notes

Reaction equation

HRID 851493 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[CH:6]=1)[CH3:3].[N+](N[C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:29]=[N:30][C:31]([CH3:35])=[C:32]([CH3:34])[CH:33]=2)=[CH:22][N:21]=1)([O-])=O>N1C=CC=CC=1>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([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][C:31]([CH3:35])=[C:32]([CH3:34])[CH:33]=3)=[CH:22][N:21]=2)[CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 127838315-(5,6-Dimethyl-3-pyridylmethyl)-2-nitroamino4-pyrimidoneHCID 132773272-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamine

Product 1

HCID 132926062-[2-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamino]-5-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidoneYield 40.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamine (1 g) and 2-nitroamino-5-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidone (1.11 g) in pyridine (3 ml) was heated under reflux for 5 hours and evaporated to dryness in vacuo. The residue was purified by chromatography on silica gel eluted with 20% methanol/chloroform followed by recrystallisation from acetonitrile/water 1:1 to give 2-[2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamino]-5-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidone (0.72 g) m.p. 72°-78°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customevaporated to dryness in vacuo
  4. customThe residue was purified by chromatography on silica gel
  5. washeluted with 20% methanol/chloroform
  6. customfollowed by recrystallisation from acetonitrile/water 1:1

Sources & evidence

ORD record
ord-a494372cc27544dea81cca4024029f3a
Source dataset
uspto-grants-1983_05
Patent number
US04385058

Reaction notes

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