5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 13137363, compound

HRID 2166700Notes

Reaction equation

HRID 2166700 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[O:28][C:29]([CH2:32][N:33]([CH3:35])[CH3:34])=[CH:30][CH:31]=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[O:28][C:29]([CH2:32][N:33]([CH3:34])[CH3:35])=[CH:30][CH:31]=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 13137346HCID 13137346, compound

Product 1

HCID 13137363HCID 13137363, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(5-dimethylaminomethyl-2-furanylmethylthio)ethylamine (1.29 g) and 2-nitroamino-5-(5-dimethylaminomethyl-2-furanylmethyl)-4-pyrimidone in pyridine (15 ml) was heated under reflux for about 20 hr. The pyridine was evaporated at reduced pressure. The last traces of pyridine were removed by azeotroping with water and water removed by azeotroping with n-propanol. The oily residue was chromatographed on a silica gel column eluting with methanol in ethyl acetate (10% v/v). Evaporation of the eluant yielded 2-[2-(5-dimethylaminomethyl-2-furanylmethylthio)ethylamino]-5-(5-dimethylaminomethyl-2-furanylmethyl)-4-pyrimidone as an oil which was converted to its trihydrochloride using an excess of ethanolic HCl. The salt was recrystallised from isopropanol yielding a white solid (0.72 g) m.p. 181°-183° C.

Workup

  1. temperatureunder reflux for about 20 hr
  2. customThe pyridine was evaporated at reduced pressure
  3. customThe last traces of pyridine were removed
  4. customby azeotroping with water and water
  5. customremoved
  6. customby azeotroping with n-propanol
  7. customThe oily residue was chromatographed on a silica gel column
  8. washeluting with methanol in ethyl acetate (10% v/v)
  9. customEvaporation of the eluant

Sources & evidence

ORD record
ord-8329ebea82264fdfbd8e69120e63b925
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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