1,1'-Thiocarbonyldi-2(1H)-pyridone → 4-Isothiocyanato-6-phenoxypyrimidine

HRID 1875925Notes

Reaction equation

HRID 1875925 reaction equation
[O:1]([C:8]1[N:13]=[CH:12][N:11]=[C:10]([NH2:14])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:16]>C(Cl)Cl>[N:14]([C:10]1[CH:9]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:13]=[CH:12][N:11]=1)=[C:15]=[S:16]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 574765666-Phenoxypyrimidin-4-amine

Product 1

HCID 574765674-Isothiocyanato-6-phenoxypyrimidineYield 192.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-phenoxypyrimidin-4-amine (0.288 g, 1.538 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (0.357 g, 1.538 mmol) in DCM was stirred at rt for 18 h. The pale orange mixture was purified by silica gel chromatography (5-35% ethyl acetate-hexanes) to afford 4-isothiocyanato-6-phenoxypyrimidine (0.55 g, 2.96 mmol, 85% yield) a yellow oil. LCMS R.T.=2.78; [M+H]+=229.94.

Workup

  1. customThe pale orange mixture was purified by silica gel chromatography (5-35% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-d44f4adc590c442595330061d795f963
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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