4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → 2-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-5-(1-n-butyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one

HRID 1719542Notes

Reaction equation

HRID 1719542 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[N+](N[C:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:29]=[CH:28][N:27]([CH2:30][CH2:31][CH2:32][CH3:33])[C:26](=[O:34])[CH:25]=2)=[CH:18][N:17]=1)([O-])=O>N1C=CC=CC=1>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:29]=[CH:28][N:27]([CH2:30][CH2:31][CH2:32][CH3:33])[C:26](=[O:34])[CH:25]=2)=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 184701322-Nitroamino-5-(1-n-butyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one

Product 1

HCID 544582212-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-5-(1-n-butyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(5-Methyl-4-imidazolylmethylthio)ethylamine (1.37 g) and 2-nitroamino-5-(1-n-butyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (2.39 g) were refluxed in pyridine (12 ml) for 17 hours. The reaction mixture was evaporated under reduced pressure and the residue washed with hot water. The mixture was allowed to cool and the water was decanted to give the title compound as a residue. Ethanolic HCl was added with warming and on subsequent cooling the trihydrochloride salt of 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(1-n-butyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one was obtained as a solid (2.50 g); recrystallisation from ethanolic HCl afforded material, m.p. 170°-173.5° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. washthe residue washed with hot water
  3. temperatureto cool
  4. customthe water was decanted

Sources & evidence

ORD record
ord-e48b5bd5e47d4b7291a6653fb1470390
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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