5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → 2-{2-[(5-Dimethylaminomethyl-2-furyl)methylthio]ethylamino}-5-nitro-4(3H)-pyrimidone

HRID 622784Notes

Reaction equation

HRID 622784 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].CS[C:17]1[N:22]=[C:21]([OH:23])[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1>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:17]2[NH:22][C:21](=[O:23])[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 178503473C5H5N3O3S

Product 1

HCID 143267002-{2-[(5-Dimethylaminomethyl-2-furyl)methylthio]ethylamino}-5-nitro-4(3H)-pyrimidoneYield 78.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethylamine (4.72 g; 22.0 mmoles) and 2-methylthio-5-nitro-4-hydroxypyrimidine (4.0 g; 21.37 mmoles) in 20 ml of ethanol was heated at reflux temperature for 18 hours. The reaction mixture was evaporated under reduced pressure, and the residue was recrystallized from 2-methoxyethanol to give 5.96 g of the title compound, mp 201°-204° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 18 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customthe residue was recrystallized from 2-methoxyethanol

Sources & evidence

ORD record
ord-041145354983440e99557e7abec3833f
Source dataset
uspto-grants-1988_09
Patent number
US04772704

Reaction notes

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