4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 13137369, compound

HRID 2166702Notes

Reaction equation

HRID 2166702 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:25]=[N:26][C:27]([CH2:30][N:31]([CH3:33])[CH3:32])=[CH:28][CH:29]=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:25]=[N:26][C:27]([CH2:30][N:31]([CH3:32])[CH3:33])=[CH:28][CH:29]=2)=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 13137349HCID 13137349, compound

Product 1

HCID 13137369HCID 13137369, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-(5-methyl-4-imidazolylmethylthio)ethylamine (1.37 g), 2-nitroamino-5-(6-dimethylaminomethyl-3-pyridylmethyl)-4-pyrimidone (2.28 g) in pyridine were heated under reflux for 22 hr. The pyridine (12 ml) was evaporated at reduced pressure yielding [2-(5-methyl-4-imidazolyl-methylthio)ethylamino]-5-(6-dimethylaminomethyl-3-pyridylmethyl)-4-pyrimidone as a brown oily residue washed with water by decantation. The residue was dissolved in dilute ethanolic hydrochloric acid and the excess of solvent evaporated at reduced pressure. The residue was recrystallised from methanol/dilute ethanolic hydrochloric acid and then twice from methanol/ethanol to yield the tetrahydrochloride (0.82 g) as a light buff solid m.p. 167°-170° C.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 22 hr
  3. customThe pyridine (12 ml) was evaporated at reduced pressure

Sources & evidence

ORD record
ord-a97e36f5930f4cd195796848c32c15fe
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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