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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1487683Generated: October 31, 2026

Tetrahydro-4H-pyran-4-ol → HCID 86726510, compound

https://huagongshe.com/reaction/1487683

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydro-4H-pyran-4-olHCID 74956—
ReactantSodium t-butoxideHCID 23676156—
ReactantHCID 86726509HCID 86726509—
SolventDichloromethaneHCID 6344—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 86726510HCID 8672651089%

Reaction Conditions

Temperature70 °C

Reaction Steps

A solution of 4-(2,4-dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylbenzamide (1 equiv), tetrahydro-2H-pyran-4-ol (1.1 equiv), and sodium tert-butoxide (1.2 equiv) in 1,4-dioxane (0.22 M) were combined in a sealable flask. The reaction mixture was put under a nitrogen atmosphere, the sealable flask was sealed, and the mixture was stirred at 70° C. for 16 h. The mixture was cooled to room temperature and concentrated to afford an oil, which was suspended in DCM and purified using flash chromatography (0-50% ethyl acetate in hexane) to afford the desired product (89% yield) as a clear oil. MS (ESI) m/z 517.5 [M+1]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09428509B2
Source datasetuspto-grants-2016_08
ORD IDord-120324a930914f298b53a746a3e4f717
Source noteuspto-grants-2016_08