Pyridine → HCID 70354167, compound

HRID 1719556Notes

Reaction equation

HRID 1719556 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[CH:6]=1)[CH3:3].[N+](N[C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:33]=[CH:32][N:31]([CH3:34])[C:30](=[O:35])[CH:29]=2)=[CH:22][N:21]=1)([O-])=O.N1C=CC=CC=1>C(O)C>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH:15][C:20]2[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]3[CH:33]=[CH:32][N:31]([CH3:34])[C:30](=[O:35])[CH:29]=3)=[CH:22][N:21]=2)[CH:6]=1)[CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 132773272-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamineHCID 70354123HCID 70354123, compound

Product 1

HCID 70354167HCID 70354167, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-[4-(Dimethylaminomethyl)pyrid-2-ylmethylthio]ethylamine (0.63 g) and 2-nitroamino-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (0.69 g) were refluxed in ethanol (12 ml) for 72 hours. As the reaction was not complete, the ethanol was replaced by pyridine (12 ml) and the solution refluxed for a further 6 hours. The reaction mixture was evaporated under reduced pressure to afford a residue which was washed with diethyl ether and recrystallised from isopropanol/ether to give 2-[2-[4-(dimethylaminomethyl)pyrid-2-ylmethylthio]ethylamino]-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (0.62 g), m.p. 137°-139° C.

Workup

  1. temperaturethe solution refluxed for a further 6 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customto afford a residue which
  4. washwas washed with diethyl ether
  5. customrecrystallised from isopropanol/ether

Sources & evidence

ORD record
ord-017bc906395140209770903224f03558
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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