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

HRID 1719536Notes

Reaction equation

HRID 1719536 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]([CH3:30])[C:26](=[O:31])[CH:25]=2)=[CH:18][N:17]=1)([O-])=O>C(O)C>[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]([CH3:30])[C:26](=[O:31])[CH:25]=2)=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 70354123HCID 70354123, compound

Product 1

HCID 703539462-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-oneYield 55.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(5-Methyl-4-imidazolylmethylthio)ethylamine (1.37 g) and 2-nitroamino-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (2.08 g) were refluxed in ethanol (10 ml) for 24 hours. The reaction mixture was cooled and evaporated under reduced pressure to afford a glassy residue which was washed with hot water yielding a white solid. This solid was filtered off, washed with water and recrystallised from methanol to yield 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (1.61 g); recrystallisation from aqueous methanol afforded the title compound, m.p. 202.5°-203.5° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated under reduced pressure
  3. customto afford a glassy residue which
  4. washwas washed with hot water yielding a white solid
  5. filtrationThis solid was filtered off
  6. washwashed with water
  7. customrecrystallised from methanol

Sources & evidence

ORD record
ord-864a287d8d434674aac02d611e871574
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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