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Ethanol → (5-Bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethanol | HCID 702 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 2-Pyridinemethanamine | HCID 19509 | — |
| 反応物 | 5-Bromo-4-chlorothieno[2,3-d]pyrimidine | HCID 45480299 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | (5-Bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine | HCID 67381984 | 63.9% |
反応手順
A stirred mixture of 5-bromo-4-chlorothieno[2,3-d]pyrimidine (3.8 g, 15.2 mmol), ethanol (250 ml), triethylamine (2.32 ml, 16.7 mmol) and 2-aminomethylpyridine (1.72 ml, 16.7 mmol) was heated under reflux for 2.5 hours. The solution was then cooled to ambient temperature, poured into water (300 ml) and extracted with dichloromethane (3×150 ml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude product. Purification by flash chromatography (silica) eluting with ethyl acetate and 40°-60° petroleum ether (1:1) gave (5-bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine as a yellow solid (3.12 g), m.pt. 127°-129° C.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08022076B2 |
| 出典データセット | uspto-grants-2011_09 |
| ORD ID | ord-71d2c6e6e7b84271b2054899a74236be |
| 出典メモ | uspto-grants-2011_09 |