Phenyl thioxochloroformate → 2-Isothiocyanato-4-methoxy-6-methylpyrimidine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][Si](C)(C)C)[N:4]=1.C1C=CC(O[C:22](Cl)=[S:23])=CC=1>C1(C)C=CC=CC=1>[N:10]([C:5]1[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([CH3:9])[N:6]=1)=[C:22]=[S:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To 30 ml of toluene is added 4.2 g of 4-methoxy-6-methyl2-trimethylsilylaminopyrimidine and 3.5 g of phenyl chlorothionocarbonate, and the mixture is stirred for 5.5 hours while heating at about 80° C. After cooling the reaction mixture to room temperature, the precipitates are removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent, ethyl acetate:toluene =1:3) to yield 2.3 g of the title compound.
Workup
- temperatureAfter cooling the reaction mixture to room temperature
- customthe precipitates are removed by filtration
- concentrationthe filtrate is concentrated under reduced pressure
- customThe residue is purified by silica gel column chromatography (eluent, ethyl acetate:toluene =1:3)
Sources & evidence
- ORD record
- ord-dcc19f4666194856af8a9fa26385a22b
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04872901
Reaction notes
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