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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1499728Generated: October 31, 2026

Water → 4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}pyridine-2-carbonitrile

https://huagongshe.com/reaction/1499728

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
Reactant1H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 75420—
Reactant4-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrileHCID 86677641—
SolventDimethylformamideHCID 6228—
Product4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}pyridine-2-carbonitrileHCID 86677663—

Reaction Conditions

Temperature30 °C

Reaction Steps

Sodium hydride (20.0 mg, 0.50 mmol) was added to a mixture of 4-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrile (from Example 16, Step 3) (90 mg, 0.28 mmol), 4-aminopyrazolo[3,4-d]pyrimidine (from Acros Organics) (57 mg, 0.42 mmol) in N,N-dimethylformamide (4 mL) and the reaction was stirred at 30° C. overnight. The mixture was treated with water and then filtered to provide the desired product. LCMS calculated for C21H19ClN7O (M+H)+: m/z=420.1; Found: 420.1

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09199982B2
Source datasetuspto-grants-2015_12
ORD IDord-6e86ab776b2549a3815fd730d1986c89
Source noteuspto-grants-2015_12