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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 570526
Notes
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Reaction equation

HRID 570526 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 initially charged in 11 ml of absolute DMSO and the mixture was heated at 150° C. for 2 h. After cooling, the mixture was filtered through Celite and washed through 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 on a rotary evaporator. 994 mg (purity 81%, 75% of theory) of the target compound were obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through Celite
  3. washwashed through 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 on a rotary evaporator
  7. custom994 mg (purity 81%, 75% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-80b58f6d8599414dbe2821474325f108
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023849B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes