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 570526Notes

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

Participants

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

temperatureAfter cooling
filtrationthe mixture was filtered through Celite
washwashed through with ethyl acetate and THF
washThe organic phase was washed with 25% aqueous ammonia solution, saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution
dry with materialdried over sodium sulphate
concentrationconcentrated on a rotary evaporator
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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