1,1'-Thiocarbonyldi-2(1H)-pyridone → 4-(3-Chlorophenyl)-6-isothiocyanatopyrimidine

HRID 250096Notes

Reaction equation

HRID 250096 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[N:29]=[CH:28][N:27]=[C:26]([NH2:30])[CH:25]=2)[CH:21]=[CH:22][CH:23]=1>ClCCl.CN(C)C=O>[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[CH:25]=[C:26]([N:30]=[C:1]=[S:2])[N:27]=[CH:28][N:29]=2)[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 57476588HCID 57476588, compound

Product 1

HCID 574765894-(3-Chlorophenyl)-6-isothiocyanatopyrimidine

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a bright orange solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (0.486 g, 2.091 mmol) in dichloromethane/N,N-dimethylformamide at room temperature was added 6-(3-chlorophenyl)pyrimidin-4-amine (0.43 g, 2.091 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-(3-chlorophenyl)-6-isothiocyanatopyrimidine (0.12 g, 0.484 mmol, 23% yield) as an orange oil. LCMS R.T.=2.15; [M]+=248.31.

Sources & evidence

ORD record
ord-82598fdf500a4920878a7c06e1afd231
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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