5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one → 2-[4-(4-Dimethylaminomethyl-2-pyridyl)butylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone

HRID 851491

Reaction equation

HRID 851491 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][CH2:12][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]([CH3:34])=[CH:32][CH:33]=2)=[CH:22][N:21]=1)([O-])=O>N1C=CC=CC=1>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][CH2:12][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]([CH3:34])=[CH:32][CH:33]=3)=[CH:22][N:21]=2)[CH:6]=1)[CH3:3]

Participants

4

Reactant 2

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 202390724-(4-Dimethylaminomethyl-2-pyridyl)butylamine

Product 1

HCID 132926082-[4-(4-Dimethylaminomethyl-2-pyridyl)butylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidoneYield 43.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-(4-dimethylaminomethyl-2-pyridyl)butylamine (1 g) and 2-nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone (1.26 g) in pyridine (5 ml) was refluxed for 4.5 hours. The solvent was removed in vacuo, the residue chromatographed and then crystallised from ethanol:ether (1:10) to yield 2-[4-(4-dimethylaminomethyl-2-pyridyl)butylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone (0.86 g) m.p. 135°-137°.

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue chromatographed
  4. customcrystallised from ethanol:ether (1:10)

Sources & evidence

ORD record
ord-4939f0473a03429eb25a482eb55e7d6f
Source dataset
uspto-grants-1983_05
Patent number
US04385058

Linked notes

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