Toluene → HCID 69313650, compound

HRID 271089Notes

Reaction equation

HRID 271089 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:9]=1[O:10][C:11]1[N:16]=[C:15]2[N:17]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:18]=[C:19](I)[C:14]2=[CH:13][N:12]=1.[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[F:7][C:8]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:9]=1[O:10][C:11]1[N:16]=[C:15]2[N:17]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:18]=[C:19]([CH:1]=[CH:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:14]2=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 11430Potassium CarbonateHCID 598343496-(2,4-Difluorophenoxy)-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 69313650HCID 69313650, compound

Conditions

Temperature
65 °C

Procedure

Tris(dibenzylidine acetone)dipalladium CHCl3 (5.0 mg, 0.004 mmol), and potassium carbonate (26 mg, 0.19 mmol) were suspended in 1 mL of toluene under argon. A solution of 6-(2,4-Difluoro-phenoxy)-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine (48 mg, 0.09 mmol) in 2 mL toluene was added, and the reaction mixture was stirred at 65° C. for 16 hours, then stirred at 110° C. for four hours. The reaction mixture was cooled, filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (23 mm×14 cm silica with hexanes/EtOAc 20:1 to 4:1) to yield 42 mg of 6-(2,4-Difluoro-phenoxy)-3-styryl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine.

Workup

  1. stirringstirred at 110° C. for four hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (23 mm×14 cm silica with hexanes/EtOAc 20:1 to 4:1)

Sources & evidence

ORD record
ord-2177491fefe5497e8fd97d06f14a6890
Source dataset
uspto-grants-2008_11
Patent number
US07452880B2

Reaction notes

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