5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one → 2-[3-(Pyrid-2-ylamino)propylamino]-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone

HRID 1906541Notes

Reaction equation

HRID 1906541 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[N+](N[C:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[CH:18][N:17]=1)([O-])=O>N1C=CC=CC=1>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 10606924N-(3-aminopropyl)pyridin-2-amine

Product 1

HCID 143973762-[3-(Pyrid-2-ylamino)propylamino]-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidoneYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(3-Aminopropylamino)pyridine (1.74 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone (2.0 g) were heated together under reflux in pyridine (8 ml) for 22 hr. The mixture was stripped, the residue triturated with ether and then water (the pH of which was adjusted to 6.5 with dilute acetic acid) to give a white solid. Recrystallisation from isopropanol gave 2-[3-(pyrid-2-ylamino)propylamino]-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone, (1.87 g; 70%), m.p. 163°-165° C.

Workup

  1. customthe residue triturated with ether
  2. customto give a white solid
  3. customRecrystallisation from isopropanol

Sources & evidence

ORD record
ord-ace70d7ad007472a84da9b1bd14a0ac1
Source dataset
uspto-grants-1987_03
Patent number
US04652650

Reaction notes

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