2,2,2-Trifluoroethanol → 4-(4-(2,6-dimethyl-4-(pyridin-4-yl)phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzonitrile

HRID 386646Notes

Reaction equation

F[C:2](F)(F)C(O)=O.[CH3:8][C:9]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH:23]=[C:22]([CH3:32])[C:10]=1[O:11][C:12]1[C:13]2N[N:20]=[N:19][C:14]=2[N:15]=[C:16](Cl)[N:17]=1.[NH2:33][C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=1.FC(F)(F)CO>>[CH3:8][C:9]1[CH:25]=[C:24]([C:26]2[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=2)[CH:23]=[C:22]([CH3:32])[C:10]=1[O:11][C:12]1[N:17]=[C:16]([NH:33][C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=2)[N:15]=[C:14]2[NH:19][N:20]=[CH:2][C:13]=12

Participants

Reactant 4

HCID 64092,2,2-Trifluoroethanol

HCID 6422Trifluoroacetic acid

HCID 133964-Aminobenzonitrile

HCID 178422825HCID 178422825, compound

Product 1

HCID 441239894-(4-(2,6-dimethyl-4-(pyridin-4-yl)phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzonitrile

Conditions

Temperature: 90 °C

Procedure

Trifluoroacetic acid (8 eq) is added to a suspension of 7-(2,6-dimethyl-4-(pyridin-4-yl)phenoxy)-5-chloro-1H-[1,2,3]triazolo[4,5-d]pyrimidine (1 eq) and 4-aminobenzonitrile (4 eq) in 2,2,2-trifluoroethanol (1 ml/0.1 mmol) in a sealed tube. The resulting mixture is heated at 90° C. for 3 days. The reaction is cooled to room temperature, concentrated to dryness and purified by silica gel chromatography.

Workup

temperatureThe reaction is cooled to room temperature
concentrationconcentrated to dryness
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-6f5a18608c6e494c95a1b72620d8c01c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372852B2

Reaction notes

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