Ethyl Acetate → 1-(2,3-Difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile

HRID 570532Notes

Reaction equation

[F:1][C:2]1[C:19]([F:20])=[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:22]#[N:23].C(OCC)(=O)C>CS(C)=O>[F:1][C:2]1[C:19]([F:20])=[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:22]#[N:23])=[N:6]1

Participants

Conditions

Temperature: 150 °C

Procedure

1.360 g (3.35 mmol) of 1-(2,3-difluorobenzyl)-3-iodo-6-methyl-1H-pyrazolo[3,4-d]pyrimidine and 330 mg (3.68 mmol) of copper(I) cyanide were initially charged in 10 ml of absolute DMSO and the mixture was heated at 150° C. for 2 h. After cooling, the mixture was added to 200 ml of ethyl acetate and washed with a mixture of concentrated aqueous ammonia solution and semisaturated aqueous ammonium chloride solution (v/v=1:3). The organic phase was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated on a rotary evaporator. 1.040 g (purity 92%, 100% of theory) of the target compound were obtained.

Workup

temperatureAfter cooling
washwashed with a mixture of concentrated aqueous ammonia solution
washThe organic phase was washed with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulphate
concentrationconcentrated on a rotary evaporator
custom1.040 g (purity 92%, 100% of theory) of the target compound were obtained

Sources & evidence

ORD record: ord-5e113ec8b2094e2bbc0bc12a7b5ba732
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023849B2

Reaction notes

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