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5-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine → (+/-)-4-(2,4-Bis(1,1-dimethylethoxy)pyrimidin-5-yl)-7-ethyl-2-methyl-9,10-dihydro-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-ol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 5-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine | HCID 818851 | — |
| 反応物 | 7-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one | HCID 22003584 | — |
| 反応物 | Butyllithium | HCID 178418339 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | (+/-)-4-(2,4-Bis(1,1-dimethylethoxy)pyrimidin-5-yl)-7-ethyl-2-methyl-9,10-dihydro-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-ol | HCID 70113732 | — |
反応手順
A stirred solution of the product from example 1 step (vi) (3.60 g) in tetrahydrofuran (30 ml) at −70° C. was treated dropwise with n-butyllithium (4.75 ml of a 2.5M solution in hexanes) and stirred for 30 minutes. A solution of the product from example 3 step (vi) (2.60 g) in tetrahydrofuran (30 ml) was added dropwise and the reaction stirred at room temperature for 3 hours. The reaction was partitioned between brine and ethyl acetate and the organics dried (MgSO4) and evaporation under reduced pressure gave a brown oil. Purification was by column chromatography eluting with 50% ethyl acetate in isohexane.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06218376B1 |
| 出典データセット | uspto-grants-2001_04 |
| ORD ID | ord-de09f20e06da4423975a7f432516d2af |
| 出典メモ | uspto-grants-2001_04 |