5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → Lupitidine

HRID 1719144Notes

Reaction equation

HRID 1719144 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].[CH3:15][C:16]1[N:21]=[CH:20][C:19]([CH2:22][C:23]2[C:24](=[O:31])[NH:25][C:26](SC)=[N:27][CH:28]=2)=[CH:18][CH:17]=1>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:26]2[NH:25][C:24](=[O:31])[C:23]([CH2:22][C:19]3[CH:20]=[N:21][C:16]([CH3:15])=[CH:17][CH:18]=3)=[CH:28][N:27]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 127838272-methylthio-5-(2-methylpyrid-5-ylmethyl)-1H-pyrimid-4-one

Product 1

HCID 4375468Lupitidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamine (1.30 g), 5-(6-methyl-3-pyridylmethyl)-2-methylthio-4-pyrimidone (1.41 g) and pyridine (10 ml) was heated under reflux for 46 hours and evaporated to dryness. The residue was washed with hot water to give 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone as an oil and this oil was treated with excess of hydrogen chloride in ethanol and evaporated to dryness. The residue was recrystallised from aqueous ethanol containing HCl to give 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone trihydrochloride m.p. 210°-213°. A sample recrystallised a further time from aqueous ethanol containing HCl had m.p. 224°-227°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 46 hours
  3. customevaporated to dryness
  4. washThe residue was washed with hot water

Sources & evidence

ORD record
ord-eb8b25344c184c7da09f8e544bd3c8d2
Source dataset
uspto-grants-1985_09
Patent number
US04539207

Reaction notes

Loading…