1,1'-Thiocarbonyldi-2(1H)-pyridone → 4-Isothiocyanato-6-(pyridin-3-yl)pyrimidine

HRID 250071Notes

Reaction equation

HRID 250071 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[N:28]=[CH:27][N:26]=[C:25]([NH2:29])[CH:24]=2)[CH:18]=1>ClCCl.CN(C)C=O>[N:29]([C:25]1[CH:24]=[C:23]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)[N:28]=[CH:27][N:26]=1)=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 574765746-(Pyridin-3-yl)pyrimidin-4-amine

Product 1

HCID 574765754-Isothiocyanato-6-(pyridin-3-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (0.682 g, 2.94 mmol) in dichloromethane/N,N-dimethylformamide at room temperature was added 6-(pyridin-3-yl)pyrimidin-4-amine (0.337 g, 1.957 mmol). The mixture was heated at 60° C. for 18 hours. LC/MS showed the desired product peak as the major peak. The deep orange mixture was purified by silica gel chromatography (1-40% ethyl acetate-hexanes) to afford 4-isothiocyanato-6-methoxypyrimidine (0.12 g, 0.56 mmol, 28.6% yield) as an orange oil.

Sources & evidence

ORD record
ord-6e077d31fc35468ea0239813870bf8c2
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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