4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 13137353, compound

HRID 2166695Notes

Reaction equation

HRID 2166695 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[S:25][C:26]([CH2:29][N:30]([CH3:32])[CH3:31])=[CH:27][CH:28]=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[S:25][C:26]([CH2:29][N:30]([CH3:31])[CH3:32])=[CH:27][CH:28]=2)=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 13137347HCID 13137347, compound

Product 1

HCID 13137353HCID 13137353, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(5-methyl-4-imidazolylmethylthio)ethylamine (1.37 g) and 2-nitroamino-5-(5-dimethylaminomethyl-2-thienylmethyl)-4-pyrimidone (2.32 g) in ethanol was heated under reflux for 48 hrs. The ethanol was evaporated at reduced pressure yielding 2-[2-(5-methyl-4-imidazolyl-methylthio)ethylamino]-5-(5-dimethylaminomethyl-2-thienylmethyl)-4-pyrimidone as a glassy residue which was washed with hot water by decantation. The residue was dissolved in isopropanol and a solution of ethanolic hydrochloric acid (3 ml) was added. Excess of solvent was removed at reduced pressure and trihydrochloride crystallized as a light buff solid (3.11 g). The solid was recrystallized from methanol-ethanol (2.36 g) 185.5°-188.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hrs
  3. customThe ethanol was evaporated at reduced pressure

Sources & evidence

ORD record
ord-4cae6c26bd174d05a8ad871b7dcef204
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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