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

HRID 1719537Notes

Reaction equation

HRID 1719537 reaction equation
[N+]([NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]([CH3:19])[C:15](=[O:20])[CH:14]=2)=[CH:7][N:6]=1)([O-])=O.[CH3:21][N:22]([CH2:24][C:25]1[O:26][C:27]([CH2:30][S:31][CH2:32][CH2:33]N)=[CH:28][CH:29]=1)[CH3:23]>C(O)C>[CH3:23][N:22]([CH2:24][C:25]1[O:26][C:27]([CH2:30][S:31][CH2:32][CH2:33][NH:4][C:5]2[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]([CH3:19])[C:15](=[O:20])[CH:14]=3)=[CH:7][N:6]=2)=[CH:28][CH:29]=1)[CH3:21]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 70354123HCID 70354123, compound

Product 1

HCID 703541222-[2-(2-Dimethylaminomethyl-5-furylmethylthio)ethylamino]-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-oneYield 43.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitroamino-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (2.08 g) and 2-(2-dimethylaminomethyl-5-furylmethylthio)ethylamine (1.82 g) were refluxed in ethanol (10 ml) for 22 hours. The reaction mixture was evaporated under reduced pressure to afford an oil which on trituration with diethyl ether gave a solid. This solid was collected by filtration, washed with diethyl ether and recrystallised from isopropanol to yield 2-[2-(2-dimethylaminomethyl-5-furylmethylthio)ethylamino]-5-(1-methyl- 2-oxopyridin-4-ylmethyl)pyrimidin-4-one (1.41 g); recrystallisation from isopropanol afforded material with m.p. 129°-132° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto afford an oil which on trituration with diethyl ether
  3. customgave a solid
  4. filtrationThis solid was collected by filtration
  5. washwashed with diethyl ether
  6. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-487370ad4a6c45208a2ba3bcaaff9c01
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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