4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → 4(1H)-Pyrimidinone, 5-((4-chlorophenyl)methyl)-2-((2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)amino)-

HRID 1856259Notes

Reaction equation

HRID 1856259 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[C:8](=[O:15])[NH:9][C:10](SC)=[N:11][CH:12]=2)=[CH:4][CH:3]=1.[CH3:18][C:19]1[NH:23][CH:22]=[N:21][C:20]=1[CH2:24][S:25][CH2:26][CH2:27][NH2:28]>>[CH3:18][C:19]1[NH:23][CH:22]=[N:21][C:20]=1[CH2:24][S:25][CH2:26][CH2:27][NH:28][C:10]1[NH:9][C:8](=[O:15])[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:17][CH:16]=2)=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 129459805-(4-Chlorobenzyl)-2-methylthiopyrimid-4-one

Product 1

HCID 30473014(1H)-Pyrimidinone, 5-((4-chlorophenyl)methyl)-2-((2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)amino)-

Procedure

An intimate mixture of 5-(4-chlorobenzyl)-2-methylthio-4-pyrimidone (17.7 g) and 2-(5-methyl-4-imidazolylmethylthio)ethylamine (11.4 g) was heated at 145°-150° for 5 hours. After cooling, the reaction mixture was triturated with water to give the free base, which was separated by decantation and recrystallised from methanol to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(4-chlorobenzyl)-4-pyrimidone m.p. 204.5°-206°.

Workup

  1. temperaturewas heated at 145°-150° for 5 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was triturated with water
  4. customto give the free base, which
  5. customwas separated by decantation
  6. customrecrystallised from methanol

Sources & evidence

ORD record
ord-8b4567b99ce54782889e5b20446531b1
Source dataset
uspto-grants-1980_08
Patent number
US04218452

Reaction notes

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