Cystamine → 2-[5-(3-Pyridylmethyl)-4-oxo-2-pyrimidylamino]ethyl disulphide

HRID 224874

Reaction equation

HRID 224874 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][S:5][CH2:6][CH2:7][NH2:8].[N+](N[C:13]1[NH:18][C:17](=[O:19])[C:16]([CH2:20][C:21]2[CH:22]=[N:23][C:24](C)=[CH:25][CH:26]=2)=[CH:15][N:14]=1)([O-])=O>C(O)C>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][C:16]2[C:17](=[O:19])[NH:18][C:13]([NH:1][CH2:2][CH2:3][S:4][S:5][CH2:6][CH2:7][NH:8][C:13]3[NH:18][C:17](=[O:19])[C:16]([CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[CH:15][N:14]=3)=[N:14][CH:15]=2)[CH:22]=1

Participants

4

Reactant 2

HCID 2915CystamineHCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one

Product 1

HCID 537906922-[5-(3-Pyridylmethyl)-4-oxo-2-pyrimidylamino]ethyl disulphide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cystamine is reacted with 2-nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone by heating in ethanol to give 2-[5-(3-pyridylmethyl)-4-oxo-2-pyrimidylamino]ethyl disulphide which is reduced with dithiothreitol to give 2-(2-mercaptoethylamino)-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone which is reacted with 5-dimethylaminomethyl-2-furylmethanol in cold aqueous hydrochloric acid to give 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone.

Sources & evidence

ORD record
ord-dd39f81c0d1049d6b4e85554e4e11c6c
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Linked notes

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