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

HRID 1499728Notes

Reaction equation

HRID 1499728 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH3:23])=[C:6]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[C:7]([O:13][CH3:14])=[C:8]([CH:10](Cl)[CH3:11])[CH:9]=1.[NH2:24][C:25]1[N:30]=[CH:29][N:28]=[C:27]2[NH:31][N:32]=[CH:33][C:26]=12.O>CN(C)C=O>[NH2:24][C:25]1[N:30]=[CH:29][N:28]=[C:27]2[N:31]([CH:10]([C:8]3[C:7]([O:13][CH3:14])=[C:6]([C:15]4[CH:20]=[CH:19][N:18]=[C:17]([C:21]#[N:22])[CH:16]=4)[C:5]([CH3:23])=[C:4]([Cl:3])[CH:9]=3)[CH3:11])[N:32]=[CH:33][C:26]=12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 866776414-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrile

Product 1

HCID 866776634-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

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

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-6e86ab776b2549a3815fd730d1986c89
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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