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(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → (4S)-4-[4-Cyano-2-(methylsulfanyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | (Methoxycarbonylsulfamoyl)triethylammonium hydroxide | HCID 11032497 | — |
| 反応物 | (4S)-4-[4-Cyano-2-(methylsulfanyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxamide | HCID 58133677 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | (4S)-4-[4-Cyano-2-(methylsulfanyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile | HCID 44133231 | — |
反応手順
The reaction was carried out under argon. (4S)-4-[4-Cyano-2-(methylsulfanyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxamide (95.0 mg, 0.213 mmol) was dissolved in THF (4 ml), and methoxycarbonylsulfamoyltriethylammonium hydroxide (Burgess reagent; 101 mg, 0.426 mmol) was added. After 30 min of stirring at room temperature, HPLC showed complete conversion. The mixture was diluted with ethyl acetate (4 ml), and water (1 ml) was added. The mixture was then applied to a Merck Extrelut® NT3 column and the filtrate was purified by preparative HPLC. Concentration of the product fractions gave 96.0 mg (quant.) of the title compound.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08691817B2 |
| 出典データセット | uspto-grants-2014_04 |
| ORD ID | ord-1506d0c660584f2ab6e2b86f16c4d421 |
| 出典メモ | uspto-grants-2014_04 |