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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 928232Generated: October 30, 2026

1,4-Dioxane → 6-(Methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine

https://huagongshe.com/reaction/928232

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,4-DioxaneHCID 31275—
ReactantPhenylboronic AcidHCID 66827—
ReactantHCID 178503373HCID 178503373—
ReactantHCID 178527066HCID 178527066—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Product6-(Methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidineHCID 17850337687.7%

Reaction Conditions

Temperature150 °C

Reaction Steps

A microwave tube was charged with 3-bromo-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (1.0 g, 4.0 mmol), phenylboronic acid (1.5 g, 12 mmol), potassium phosphonate (2.5 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0.35 g, 0.30 mmol), dioxane (16 mL) and water (4 mL). The mixture was heated in microwave at 150° C. for 20 min. The reaction mixture was poured into water. The aqueous layer was extracted with EtOAc (10×). The combined organic layer was dried (Na2SO4), concentrated, and purified to provide 6-(methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine (0.85 g, 87%) as a white solid. MS m/z 243.1 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09290499B2
Source datasetuspto-grants-2016_03
ORD IDord-fa2e1526cd40497990c1910231234df8
Source noteuspto-grants-2016_03