5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one → HCID 178424600, compound

HRID 1247900Notes

Reaction equation

HRID 1247900 reaction equation
[N+]([NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[CH:7][N:6]=1)([O-])=O.[NH:20]([C:24]1[S:25][CH:26]=[C:27]([CH2:29][S:30][CH2:31][CH2:32]N)[N:28]=1)[C:21]([NH2:23])=[NH:22]>N1C=CC=CC=1>[NH:20]([C:24]1[S:25][CH:26]=[C:27]([CH2:29][S:30][CH2:31][CH2:32][NH:4][C:5]2[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]3[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=3)=[CH:7][N:6]=2)[N:28]=1)[C:21]([NH2:23])=[NH:22]

Participants

4

Reactant 2

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178424600HCID 178424600, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone (5.21 g) and 2-(2-guanidino-4-thiazolylmethylthio)ethylamine (2.98 g) were heated under reflux in dry pyridine for 9 hours. The mixture was evaporated and the residue was washed with water to give 2-[2-(2-guanidino-4-thiazolylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone which was treated with hydrogen chloride in ethanol-ether to give the trihydrochloride (0.92 g). This was converted into the free base by dissolving the material in water, adjusting the mixture to pH 9 with sodium bicarbonate, and extracting the mixture with chloroform and evaporating the extracts to dryness. A sample of the free base recrystallised from aqueous 2-propanol had m.p. 161°-164°.

Workup

  1. customThe mixture was evaporated
  2. washthe residue was washed with water

Sources & evidence

ORD record
ord-f9eab0c29670478a84d860dad21f84cf
Source dataset
uspto-grants-1985_06
Patent number
US04521418

Reaction notes

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