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Ethanol → 5-(4-Formylphenyl)pyrimidine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethanol | HCID 702 | — |
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 4-Formylphenylboronic Acid | HCID 591073 | — |
| 反応物 | 5-Chloropyrimidine hydrochloride | HCID 22735170 | — |
| 触媒 | (Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1) | HCID 10974057 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 5-(4-Formylphenyl)pyrimidine | HCID 3861212 | 48.7% |
反応手順
1 M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of 5-chloropyrimidine hydrochloride (3.03 g, 20.06 mmol, prepared as described in WO 9821188), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.80 g (42%) of the title compound. MS 185 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06713455B2 |
| 出典データセット | uspto-grants-2004_03 |
| ORD ID | ord-ae4430c86d0f46dba2137ba2e4b21c4e |
| 出典メモ | uspto-grants-2004_03 |