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

HRID 1905889Notes

Reaction equation

HRID 1905889 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-aa126100c1014a86b52139bb4a6c1c74
Source dataset
uspto-grants-1987_03
Patent number
US04649141

Reaction notes

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