HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium borohydride → Tert-butyl 4-(5-(2-(4-fluorophenyl)-1,3-dihydroxypropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | 4-(5-(2-(4-Fluorophenyl)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate | HCID 131734231 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Tert-butyl 4-(5-(2-(4-fluorophenyl)-1,3-dihydroxypropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate | HCID 118023378 | 92.5% |
Reaction Steps
A solution of 4-(5-(2-(4-fluorophenyl)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate (700 mg, 1.5 mmol) in 20 mL of THF was cooled to −10° C., followed by the addition of LiBH4 (180 mg, 7.5 mmol) slowly. This mixture was allowed to warm to RT and stirred overnight. The reaction was quenched by MeOH (3 mL) and then concentrated in vacuo. The residue was purified by silica gel column (DCM:MeOH, 10:1) to obtain the desired product (300 mg, yield 47%) as a yellow foam. MS (ES+) C22H29FN4O4 requires: 432. found 433 [M+H]+; purity: 67% (UV254).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09200002B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-6c52516ec68441a594c8e485c993410e |
| Source note | uspto-grants-2015_12 |