5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 53653085, compound

HRID 1719543Notes

Reaction equation

HRID 1719543 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:6][C:7]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:8][CH:9]=1)[CH3:3].[N+](N[C:19]1[NH:24][C:23](=[O:25])[C:22]([CH2:26][C:27]2[CH:32]=[CH:31][N:30]([CH2:33][CH2:34][CH2:35][CH3:36])[C:29](=[O:37])[CH:28]=2)=[CH:21][N:20]=1)([O-])=O>N1C=CC=CC=1>[CH3:3][N:2]([CH2:4][C:5]1[O:6][C:7]([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[CH:32]=[CH:31][N:30]([CH2:33][CH2:34][CH2:35][CH3:36])[C:29](=[O:37])[CH:28]=3)=[CH:21][N:20]=2)=[CH:8][CH:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 184701322-Nitroamino-5-(1-n-butyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one

Product 1

HCID 53653085HCID 53653085, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(2-Dimethylaminomethyl-5-furylmethylthio)ethylamine (1.44 g) and 2-nitroamino-5-(1-n-butyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (1.76 g) were refluxed in pyridine (10 ml) for 24 hours. The reaction mixture was evaporated under reduced pressure to afford an oil which was washed with hot water. The mixture was allowed to cool overnight and the water was decanted to give the title compound as a residue. Ethanolic HCl (3 ml) and isopropanol were added with warming to give a solution which was evaporated under reduced pressure to give a residue which was recrystallised from isopropanolethanolic HCl to give 2-[2-(2-dimethylaminomethyl-5-furylmethylthio)ethylamino]-5-(1-n-butyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one as a trihydrochloride salt (2.67 g), m.p. 169°-171.5° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto afford an oil which
  3. washwas washed with hot water
  4. temperatureto cool overnight
  5. customthe water was decanted

Sources & evidence

ORD record
ord-f2246d7718324c38be6380e1be2089dd
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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