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Sodium hydride → 4-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-bromo-6-chloro-3-ethoxybenzonitrile

HRID 1499738
Notes
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Reaction equation

HRID 1499738 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[N:10][C:11]=2[NH2:13])[NH:6][N:5]=1.[Br:14][C:15]1[C:22]([O:23][CH2:24][CH3:25])=[C:21]([CH:26](Cl)[CH3:27])[CH:20]=[C:19]([Cl:29])[C:16]=1[C:17]#[N:18]>CN(C)C=O.C(Cl)Cl>[NH2:13][C:11]1[N:10]=[CH:9][N:8]=[C:7]2[N:6]([CH:26]([C:21]3[CH:20]=[C:19]([Cl:29])[C:16]([C:17]#[N:18])=[C:15]([Br:14])[C:22]=3[O:23][CH2:24][CH3:25])[CH3:27])[N:5]=[C:4]([CH3:3])[C:12]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 866776672-Bromo-6-chloro-4-(1-chloroethyl)-3-ethoxybenzonitrileHCID 178434474HCID 178434474, compound

Product 1

HCID 866776684-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-bromo-6-chloro-3-ethoxybenzonitrileYield 60%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
2×
HCID 6344DichloromethaneSolvent

Procedure

Sodium hydride (16 mg, 0.41 mmol) was added to a mixture of 3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (33 mg, 0.22 mmol) in N,N-dimethylformamide (3 mL, 40 mmol) and was stirred for 10 minutes. 2-bromo-6-chloro-4-(1-chloroethyl)-3-ethoxybenzonitrile (60 mg, 0.2 mmol) in N,N-dimethylformamide (2 mL) was added and the reaction was stirred at 50° C. overnight. The mixture was diluted with methylene chloride, washed with sat'd NaHCO3, water, brine, dried over Na2SO4, filtered and concentrated. The product was purified by flash column chromatography eluting with CH2Cl2/MeOH 0-10%, to give 4-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-bromo-6-chloro-3-ethoxybenzonitrile (0.05 gm, 60%) as a solid, LCMS calculated for C17H16BrClN6O (M+H)+: m/z=437.0, 435.0; found: 436.9, 434.7.

Workup

  1. stirringthe reaction was stirred at 50° C. overnight
  2. washwashed with sat'd NaHCO3, water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash column chromatography
  7. washeluting with CH2Cl2/MeOH 0-10%

Sources & evidence

ORD record
ord-1c508c27351745558d130b738bb4ac28
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09199982B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes