5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one → 2-[3-[N-(2-chlorobenzyl)-N-pyrid-2-ylamino]propylamino]-5-(6-methylpyrid-3-ylmethyl)-pyrimid-4-one

HRID 464355Notes

Reaction equation

HRID 464355 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13].[N+](N[C:24]1[NH:29][C:28](=[O:30])[C:27]([CH2:31][C:32]2[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=2)=[CH:26][N:25]=1)([O-])=O>N1C=CC=CC=1>[Cl:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:24]1[NH:29][C:28](=[O:30])[C:27]([CH2:31][C:32]2[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=2)=[CH:26][N:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 202073322-[N-(3-aminopropyl)-N-(2-chlorobenzyl)amino]pyridine

Product 1

HCID 540924132-[3-[N-(2-chlorobenzyl)-N-pyrid-2-ylamino]propylamino]-5-(6-methylpyrid-3-ylmethyl)-pyrimid-4-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[N-(3-aminopropyl)-N-(2-chlorobenzyl)amino]pyridine (1 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (0.78 g) were heated together under reflux in pyridine (10 ml) for 20 hr. After stripping, the residue was triturated with ether and recrystallised twice from ethanol/water to give 2-[3-[N-(2-chlorobenzyl)-N-pyrid-2-ylamino]propylamino]-5-(6-methylpyrid-3-ylmethyl)-pyrimid-4-one 0.4H2O, 0.34 g (20%) mp softens 94°-102° C. melts 120°-26° C.

Workup

  1. customthe residue was triturated with ether
  2. customrecrystallised twice from ethanol/water

Sources & evidence

ORD record
ord-874f50d226a245398080259d2ea94701
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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