2,2,2-Trifluoroethanol → 4-(7-(2,6-dimethyl-4-(pyridin-4-yl)phenoxy)-1H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamino)benzonitrile

HRID 222090Notes

Reaction equation

FC(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]2[NH:21][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: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]2[NH:21][N:20]=[N:19][C:14]=2[N:15]=[C:16]([NH:33][C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=2)[N:17]=1

Participants

Reactant 4

HCID 64092,2,2-Trifluoroethanol

HCID 6422Trifluoroacetic acid

HCID 133964-Aminobenzonitrile

HCID 178422825HCID 178422825, compound

Product 1

HCID 1784228264-(7-(2,6-dimethyl-4-(pyridin-4-yl)phenoxy)-1H-[1,2,3]triazolo[4,5-d]pyrimidin-5-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-974e846017254dddba1fbbf7a2531faa
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207178B2

Reaction notes

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