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

HRID 1719548Notes

Reaction equation

HRID 1719548 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][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:26](=[O:37])[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][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:26](=[O:37])[CH:25]=2)=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 703539322-Nitroamino-5-(1-benzyl-2-oxo-pyrid-4-ylmethyl)-4-pyrimidone

Product 1

HCID 703539962-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-5-(1-benzyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[2-(5-Methyl-4-imidazolylmethylthio)ethylamine (1.28 g) and 2-nitroamino-5-(1-benzyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (2.47 g) were refluxed in pyridine (12 ml) for 20 hours. The reaction mixture was evaporated under reduced pressure and the glassy residue washed with hot water. The mixture was allowed to cool and the water was decanted to give the title compound as a residue. This residue was taken up in isopropanol, treated with ethanolic HCl, evaporated under reduced pressure and crystallised from ethanol-methanol to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(1-benzyl-2-oxopyridin 4-ylmethyl)pyrimidin-4-one as a trihydrochloride salt (3.23 g): recrystallisation gave material with m.p. 185.5°-189° C.

Workup

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

Sources & evidence

ORD record
ord-dccf44d6d95a4c36b50cd4a550d6e789
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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