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

HRID 1499709Notes

Reaction equation

HRID 1499709 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH3:23])=[C:6]([C:15]2[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[N:19][CH:20]=2)[C:7]([O:13][CH3:14])=[C:8]([CH:10](Cl)[CH3:11])[CH:9]=1.[CH3:24][C:25]1[C:33]2[C:28](=[N:29][CH:30]=[N:31][C:32]=2[NH2:34])[NH:27][N:26]=1.O>CN(C)C=O>[NH2:34][C:32]1[N:31]=[CH:30][N:29]=[C:28]2[N:27]([CH:10]([C:8]3[C:7]([O:13][CH3:14])=[C:6]([C:15]4[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[N:19][CH:20]=4)[C:5]([CH3:23])=[C:4]([Cl:3])[CH:9]=3)[CH3:11])[N:26]=[C:25]([CH3:24])[C:33]=12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 866776495-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrileHCID 178434474HCID 178434474, compound

Product 1

HCID 866776505-{3-[1-(4-Amino-3-methyl-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 mg, 0.50 mmol) was added to a mixture of 5-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrile (90 mg, 0.28 mmol), 3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (63 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 C22H21ClN7O (M+H)+: m/z=434.1; Found: 434.2

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-dbb059da7e204f3582edc8fc2314a580
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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