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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1476173Generated: November 1, 2026

Dichloromethane → HCID 178488247, compound

https://huagongshe.com/reaction/1476173

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantSodium CarbonateHCID 10340—
Reactant(4-Fluoro-3-methoxyphenyl)boronic acidHCID 44558185—
ReactantHCID 178508725HCID 178508725—
SolventEthanolHCID 702—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductHCID 178488247HCID 17848824748.5%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.500 g, 1.91 mmoles) in DMF (8 ml), ethanol (4 ml) and water (4 ml), 4-Fluoro-3-methoxyphenyl boronic acid (0.423 g, 2.49 mmoles) and sodium carbonate (1.01 g, 9.57 mmoles) were added and the system is degassed for 30 min Tetrakis triphenylphosphine Palladium (0.436 g, 0.377 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture was celite filtered, concentrated and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol:dichloromethane to afford the title compound as yellow solid (0.240 g, 48% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 13.64(s, 1H), 8.20(s, 1H), 8.08(s, 1H), 7.54(d, J=9.3Hz, 1H), 7.34(d, J=8.3Hz, 1H),3.82(s, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09018375B2
Source datasetuspto-grants-2015_04
ORD IDord-020802df92234252a55f8b0446d3fd14
Source noteuspto-grants-2015_04