5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 13137361, compound

HRID 2166699Notes

Reaction equation

HRID 2166699 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].[N+](N[C:19]1[NH:24][C:23](=[O:25])[C:22]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][N:34]([CH3:36])[CH3:35])=[CH:29][CH:28]=2)=[CH:21][N:20]=1)([O-])=O>C(O)C>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:19]2[NH:24][C:23](=[O:25])[C:22]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][N:34]([CH3:35])[CH3:36])=[CH:29][CH:28]=3)=[CH:21][N:20]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 13137348HCID 13137348, compound

Product 1

HCID 13137361HCID 13137361, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(5-dimethylaminomethyl-2-furanylmethylthio)ethylamine (1.71 g) and 2-nitroamino-5-(4-dimethylamino methylbenzyl)-4-pyrimidone (1.97 g) in ethanol (12 ml) was heated under reflux for 42 hr. The ethanol was evaporated at reduced pressure yielding 2-[2-(5-dimethylaminomethyl-2-furanylmethylthio)ethylamino]-5-(4-dimethylaminomethylbenzyl) 4-pyrimidone as a brown oily residue which was washed with hot water, cooled and mixed with dilute ethanolic hydrochloride acid. Excess of ethanol was evaporated under reduced pressure and the residue was recrystallised from isopropanol/methanol and from ethanol to give the trihydrochloride (1.85 g) as an off-white solid m.p. 180°-184° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 42 hr
  3. customThe ethanol was evaporated at reduced pressure

Sources & evidence

ORD record
ord-a27b488ecae645f9b822662ec7bfcc6a
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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