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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2172667Generated: October 27, 2026

Aluminium lithium hydride → 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanol

https://huagongshe.com/reaction/2172667

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAluminium lithium hydrideHCID 21226445—
Reactant2-((3aR,4S,6R,6aS)-6-(7-((1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)acetic acidHCID 66575873—
SolventTetrahydrofuranHCID 8028—
Product2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanolHCID 67289290—

Reaction Conditions

Temperature-5 °C

Reaction Steps

LiAlH4 (0.2 g) was added to THF (10 vol) slowly at 0 to −10° C. To this mixture was added a solution of compound 11a (3 g) in THF (15 mL) slowly over 30 min at 0 to −10° C. The reaction mixture was stirred at 0 to −10° C. for 4-12 hrs. The reaction was monitored by TLC. When the reaction was complete, it was quenched and the product was isolated by routine work up. The filtrate was concentrated under reduced pressure, and compound 12 was isolated as an oily mass; yield 14 g, 70-75%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09056838B2
Source datasetuspto-grants-2015_06
ORD IDord-38c56e67214248f89b31cba28eb5529a
Source noteuspto-grants-2015_06