5-benzyl-6-methyl-2-methylsulfanyl-1H-pyrimidin-4-one → 5-benzyl-6-methyl-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-4-one

HRID 2419003Notes

Reaction equation

HRID 2419003 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[NH:10][CH:9]=[N:8][C:7]=1[CH3:11].[CH2:12]([C:19]1[C:20](=[O:28])[NH:21][C:22](SC)=[N:23][C:24]=1[CH3:25])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:11][C:7]1[N:8]=[CH:9][NH:10][C:6]=1[CH2:5][S:4][CH2:3][CH2:2][NH:1][C:22]1[NH:21][C:20](=[O:28])[C:19]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:24]([CH3:25])[N:23]=1

Participants

3

Reactant 2

HCID 1354225835-benzyl-6-methyl-2-methylsulfanyl-1H-pyrimidin-4-oneHCID 178433288HCID 178433288, compound

Product 1

HCID 1784332915-benzyl-6-methyl-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-4-oneYield 65.9%

Procedure

An intimate mixture of 5-(2-aminoethyl)thiomethyl-4-methylimidazole (1.28 gms) and 5-benzyl-6-methyl-2-methylthio-4-pyrimidone (1.84 gms) was heated at 150°-160° C (oil-bath temperature) for 41/2 hours. The mixture was cooled, washed with water and recrystallised from isopropanol to give 2-[-2-(4-methyl-5-imidazolylmethylthio)ethylamino]-5-benzyl-6-methyl-4-pyrimidone (1.82 gms) m.p. = 140°-141.5° C.

Workup

  1. temperaturewas heated at 150°-160° C (oil-bath temperature) for 41/2 hours
  2. temperatureThe mixture was cooled
  3. washwashed with water
  4. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-e1591ec4fce544af98b4813f31147463
Source dataset
uspto-grants-1978_08
Patent number
US04104381

Reaction notes

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