5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 13137371, compound

HRID 2166703Notes

Reaction equation

HRID 2166703 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:28]=[N:29][C:30]([CH2:33][N:34]([CH3:36])[CH3:35])=[CH:31][CH:32]=2)=[CH:21][N:20]=1)([O-])=O>N1C=CC=CC=1>[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:28]=[N:29][C:30]([CH2:33][N:34]([CH3:35])[CH3:36])=[CH:31][CH:32]=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 13137349HCID 13137349, compound

Product 1

HCID 13137371HCID 13137371, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-(5-dimethylaminomethyl-2-furanylmethylthio)ethylamine (1.71 g) and 2-nitroamino-5-(6-dimethylaminomethyl-3-pyridylmethyl)-4-pyrimidone (1.98 g) in pyridine (12 ml) was refluxed for 22 hr, allowed to cool and the pyridine evaporated at reduced pressure. The residue was washed by decantation with hot water, dissolved in dilute ethanolic hydrochloric acid, and the solvent evaporated yielding 2-[2-(5-dimethylaminomethyl-2-furanylmethylthio)ethylamino]-5-(6-dimethylaminomethyl-3-pyridylmethyl)-4-pyrimidone. The residue was recrystallised from methanol/dilute ethanolic hydrochloric acid and from methanol/ethanol to give the 3.8 hydrochloride 1.4 hydrate (0.85 g) as a light buff solid m.p. 142°-5° C. Evaporation of the mother liquors and recrystallisation of the residue from methanol/ethanol yields more product (0.62 g) m.p. 138°-142° C.

Workup

  1. temperaturewas refluxed for 22 hr
  2. temperatureto cool
  3. customthe pyridine evaporated at reduced pressure
  4. washThe residue was washed by decantation with hot water
  5. dissolutiondissolved in dilute ethanolic hydrochloric acid
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-17242fff3dcd4de5a4e278852a5489a0
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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