1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 57486220, compound

HRID 1875940Notes

Reaction equation

HRID 1875940 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH3:17][O:18][C:19]1[N:24]=[CH:23][C:22]([C:25]2[CH:30]=[C:29]([NH2:31])[N:28]=[CH:27][N:26]=2)=[CH:21][N:20]=1>ClCCl.CN(C)C=O>[N:31]([C:29]1[N:28]=[CH:27][N:26]=[C:25]([C:22]2[CH:21]=[N:20][C:19]([O:18][CH3:17])=[N:24][CH:23]=2)[CH:30]=1)=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 58088249HCID 58088249, compound

Product 1

HCID 57486220HCID 57486220, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (0.832 g, 3.58 mmol) in dichloromethane/N,N-dimethylformamide at room temperature was added 2′-methoxy-4,5′-bipyrimidin-6-amine (0.56 g, 2.76 mmol). The orange mixture was heated at 60° C. for 18 hours. The LC/MS showed the desired product peak as the major peak. The deep orange mixture was purified by silica gel chromatography (0-40% ethyl acetate-hexanes) to afford 4-isothiocyanato-6-methoxypyrimidine (0.1 g, 0.408 mmol, 15% yield) as an orange solid. LCMS R.T.=2.29; [M+H]+=246.03.

Sources & evidence

ORD record
ord-5ccd142407d745a0a4273b3978bcf40e
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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