1,1'-Thiocarbonyldi-2(1H)-pyridone → 4-(4-Chlorophenyl)-6-isothiocyanatopyrimidine

HRID 250093Notes

Reaction equation

HRID 250093 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:29]=[CH:28][N:27]=[C:26]([NH2:30])[CH:25]=2)=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:25]=[C:26]([N:30]=[C:1]=[S:2])[N:27]=[CH:28][N:29]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 574765876-(4-Chlorophenyl)pyrimidin-4-amine

Product 1

HCID 574765864-(4-Chlorophenyl)-6-isothiocyanatopyrimidine

Conditions

Temperature
60 °C

Procedure

To a bright orange solution of 1,1′-thiocarbonyldipyridin-2(1H)-one(0.666 g, 2.87 mmol) dichloromethane/N,N-dimethylformamide at room temperature was added 6-(4-chlorophenyl)pyrimidin-4-amine (0.59 g, 2.87 mmol). The orange mixture was heated at 60° C. for 18 hours. The LC/MS showed the desired product peak as a major peak. The deep orange mixture was purified by silica gel chromatography (0-40% ethyl acetate-hexanes) to afford 4-(4-chlorophenyl)-6-isothiocyanatopyrimidine (0.322 g, 1.300 mmol, 45% yield) as an orange oil. LCMS R.T.=2.82; [M]+=248.03.

Sources & evidence

ORD record
ord-21b742fb7bfc486394d8372fd0d924ca
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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