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1-(2-Fluorobenzyl)-3-iodo-6-methyl-1H-pyrazolo[3,4-d]pyrimidine → 1-(2-Fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile

HRID 536499
Notes
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Reaction equation

HRID 536499 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7](I)=[N:6]1.[Cu][C:21]#[N:22]>CS(C)=O>[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:21]#[N:22])=[N:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 712854301-(2-Fluorobenzyl)-3-iodo-6-methyl-1H-pyrazolo[3,4-d]pyrimidineHCID 178418546HCID 178418546, compound

Product 1

HCID 712856751-(2-Fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

1.485 g (4.03 mmol) of 1-(2-fluorobenzyl)-3-iodo-6-methyl-1H-pyrazolo[3,4-d]pyrimidine and 397 mg (4.44 mmol) of copper(I) cyanide were put in 11 ml of absolute DMSO and heated for 2 h at 150° C. After cooling, the reaction mixture was filtered on Celite and then washed with ethyl acetate and THF. The organic phase was washed with 25% aqueous ammonia solution, saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated in a rotary evaporator. 994 mg (purity 81%, 75% of theor.) of the target compound was obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered on Celite
  3. washwashed with ethyl acetate and THF
  4. washThe organic phase was washed with 25% aqueous ammonia solution, saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in a rotary evaporator
  7. custom994 mg (purity 81%, 75% of theor.) of the target compound was obtained

Sources & evidence

ORD record
ord-b803718696d947808e5db3312937711f
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859569B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes