5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → 2-[2-(2-Dimethylaminomethyl-5-furylmethylthio)ethylamino]-5-(1-benzyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one

HRID 1719549Notes

Reaction equation

HRID 1719549 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][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:29](=[O:40])[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][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:29](=[O:40])[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 703539322-Nitroamino-5-(1-benzyl-2-oxo-pyrid-4-ylmethyl)-4-pyrimidone

Product 1

HCID 703539112-[2-(2-Dimethylaminomethyl-5-furylmethylthio)ethylamino]-5-(1-benzyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-oneYield 83.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(2-Dimethylaminomethyl-5-furylmethylthio)ethylamine (2.28 g) and 2-nitroamino-5-(1-benzyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (2.80 g) were refluxed in pyridine (12 ml) for 20 hours. The reaction mixture was evaporated under reduced pressure and the resultant oily residue was washed with hot water. The mixture was allowed to cool and the water was washed twice with cold water and recrystallised from isopropanol to yield 2-[2-(2-dimethylaminomethyl-5-furylmethylthio)ethylamino]-5-(1-benzyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (3.33 g), m.p. 95.5°-98° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. washthe resultant oily residue was washed with hot water
  3. temperatureto cool
  4. washthe water was washed twice with cold water
  5. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-5b1fef2c07254fb0acbd6c88f49a85e7
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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