関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 1,2,3,4-Tetrahydroquinoline | HCID 69460 | — |
| 反応物 | 2-Chloro-1-methylpyridinium iodide | HCID 167069 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | 4-(2,5-Dichloro-phenoxy)-pyrimidine-5-carboxylic acid | HCID 67320261 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | HCID 53311618 | HCID 53311618 | 2% |
反応手順
To a solution of 200 mg (0.7 mmol) 4-(2,5-dichloro-phenoxy)-pyrimidine-5-carboxylic acid in 2 mL dichloromethane were added 197 mg (0.77 mmol) 2-chloro-1-methylpyridinium iodide (commercially available, CAS RN 14338-32-0), 0.2 mL (1.4 mmol) triethylamine and 103 mg (0.77 mmol) 1,2,3,4-tetrahydroquinoline (commercially available, CAS RN 635-46-1). The solution was stirred 2 hours at room temperature. The reaction mixture was poured on saturated aqueous sodium bicarbonate solution and extracted three times with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated under vacuum. The residue was purified by preparative HPLC (Phenomenex Gemini column) using a gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2) to give 5.6 mg (2%) of the desired compound. MS (ESI): m/z=400.2 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08729091B2 |
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| 出典データセット | uspto-grants-2014_05 |
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| ORD ID | ord-d8ec0e8fc8444cdb88693c93b84f2b27 |
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| 出典メモ | uspto-grants-2014_05 |
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