5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 20277867, compound

HRID 1248415Notes

Reaction equation

HRID 1248415 reaction equation
CS[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][N:4]=1.[NH2:16][CH2:17][CH2:18][S:19][CH2:20][C:21]1[O:25][C:24]([CH2:26][N:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=1>>[CH3:29][N:27]([CH2:26][C:24]1[O:25][C:21]([CH2:20][S:19][CH2:18][CH2:17][NH:16][C:3]2[NH:8][C:7](=[O:9])[C:6]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:5][N:4]=2)=[CH:22][CH:23]=1)[CH3:28]

Participants

3

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 155896822-(Methylsulfanyl)-5-phenylpyrimidin-4(3H)-one

Product 1

HCID 20277867HCID 20277867, compoundYield 79.2%

Procedure

A mixture of 2-(methylthio)-5-phenyl-4(3H)-pyrimidinone (1.09 g) and 5-[[(2-aminoethyl)thio]methyl]-N,N-dimethyl-2-furanmethanamine (2.14 g) was heated at 140° for 4 h. The cooled residue was chromatographed (silica/ethyl acetate-methanol, 1:1) to give a product which was crystallised from methyl acetate-light petroleum (b.p. 60°-80°) yielding the title compound (1.52 g) m.p. 116°-118°.

Workup

  1. temperaturewas heated at 140° for 4 h
  2. customThe cooled residue was chromatographed (silica/ethyl acetate-methanol, 1:1)
  3. customto give a product which
  4. customwas crystallised from methyl acetate-light petroleum (b.p. 60°-80°)

Sources & evidence

ORD record
ord-8b82a35654aa49d3bb735f5a0a6a6558
Source dataset
uspto-grants-1985_06
Patent number
US04524071

Reaction notes

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