HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aluminium lithium hydride → 4-{5-[5-Methyl-2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-thiophen-2-yl}-butan-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | 4-{5-[5-Methyl-2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-thiophen-2-yl}-butyric acid methyl ester | HCID 57936148 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-{5-[5-Methyl-2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-thiophen-2-yl}-butan-1-ol | HCID 11200481 | — |
Reaction Steps
The ester from Step B (37 mg, 0.09 mmol) was dissolved in 1 ml of THF and LAH (1M in THF, 0.22 ml, 0.22 mmol) was added. After 30 minutes, the mixture was quenched with water and extracted with ether. The organic layers were washed with brine, dried over sodium sulfate and evaporated. The crude product was purified by preparative HPLC. Yield: 15 mg (43%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07615562B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-cd8ece670e464abf89f388607553056d |
| Source note | uspto-grants-2009_11 |