HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → N-acetyl-N-[4-(4-acetyl-2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | N-acetyl-N-[4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide | HCID 89488219 | — |
| Product | N-acetyl-N-[4-(4-acetyl-2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide | HCID 89488227 | 46% |
Reaction Steps
To a mixture of N-acetyl-N-[4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide (158 mg, 0.43 mmol, 1 eq) in 3 mL of ethanol is added sodium borohydride (35 mg, 0.94 mmol, 2.2 eq). The mixture is refluxed for 1 h. The mixture is then poured into water, extracted with dichloromethane (3×50 mL), dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material is purified by column chromatography using silica gel in heptane and ethyl acetate (1:0 to 0:1) as eluent and 66 mg (46%) of N-acetyl-N-[4-(4-acetyl-2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide are obtained as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09023844B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-cbe0b4a2536f4ac0900ca83b08c5a10a |
| Source note | uspto-grants-2015_05 |