Sodium Bicarbonate → 1-(2-Fluorobenzyl)-4-(2-thienyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine

HRID 1865906Notes

Reaction equation

HRID 1865906 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[N:10]=[CH:11][C:3]=12.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1B(O)O.C([O-])(O)=O.[Na+]>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][N:9]1[C:4]2=[N:5][C:6]([NH2:8])=[N:7][C:2]([C:21]3[S:20][CH:24]=[CH:23][CH:22]=3)=[C:3]2[CH:11]=[N:10]1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 220155054-chloro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine

Product 1

HCID 220154931-(2-Fluorobenzyl)-4-(2-thienyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amineYield 20%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-chloro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (139 mg, 0.5 mmol) in dry THF (10 mL) was treated with 2-thiopheneboronic acid (128 mg, 1.0 mmol), Pd(PPh3)4 (50 mg, 10 mol %) and saturated aqueous NaHCO3 solution (2 mL), refluxed for 30 min, diluted with H2O, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo. The resulting dark brown oil was purified by chromatography [SiO2; heptane:EtOAc (1:1) then (1:3)] to give the title compound (32 mg, 20%) as a cream solid.

Workup

  1. temperaturerefluxed for 30 min
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting dark brown oil was purified by chromatography [SiO2

Sources & evidence

ORD record
ord-72d2283d5d3a4812b5ce7b17690ef642
Source dataset
uspto-grants-2009_12
Patent number
US07629349B2

Reaction notes

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