(3-Fluoro-5-phenylmethoxyphenyl)boronic acid → 3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 634425Notes

Reaction equation

HRID 634425 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[CH2:12]([O:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[C:24]([F:26])[CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:11])[NH:4][N:3]=2)[CH:23]=[C:24]([F:26])[CH:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 44558161(3-Fluoro-5-phenylmethoxyphenyl)boronic acidHCID 178508725HCID 178508725, compound

Product 1

HCID 1785087223-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 33.1%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (6.10 mmol 1.591 g), (3-(benzyloxy)-5-fluorophenyl)boronic acid (4.06 mmol 1.0 g), dppf (0,610 mmol, 338 mg) Potassium phosphate anhydrous (10.16 mmol, 2.157 g) were suspended in dioxane and the mixture was heated at 180 C for 25 min in a Mw reactor then poured in 100 ml of water. The mixture was stirred overnight then filtered on a buchner funnel washing with 30 ml of water. The crude material was purified by chromatography eluting with DCM\ MeOH (80/20) in DCM to give the title compound (450 mg, 1.342 mmol, 33% yield) as a beige solid.

Workup

  1. temperaturethe mixture was heated at 180 C for 25 min in a Mw reactor
  2. filtrationthen filtered on a buchner funnel
  3. washwashing with 30 ml of water
  4. customThe crude material was purified by chromatography
  5. washeluting with DCM\ MeOH (80/20) in DCM

Sources & evidence

ORD record
ord-5b06a4124b9b4bc8a5550e4682b7ff16
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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