HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → [6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester | HCID 86680319 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | [6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol | HCID 90014303 | 105.6% |
Reaction Steps
A solution of 139 mg 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]-pyridine-4-carboxylic acid ethyl ester in 8 ml of dry THF was cooled to −20° C. and 18 mg of lithium borohydride was added. After 10 min at −20° C., the reaction was slowly brought to rt. After 1.5 h at rt water and ethyl acetate were added to the reaction. The phases were separated and the organic phase was dried over sodium sulphate, filtrated and concentrated in vacuo to obtain 130 mg (98%) of the title compound as a crude product, which was used without purification in the subsequent step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133181B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-15a7df36057c4b7da991245f2e32e5fd |
| Source note | uspto-grants-2015_09 |