Sodium Carbonate → 5-Biphenyl-4-yl-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine

HRID 19607Notes

Reaction equation

HRID 19607 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([S:14][CH3:15])[N:11]3[N:16]=[CH:17][CH:18]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:2]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([S:14][CH3:15])[N:11]3[N:16]=[CH:17][CH:18]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid2×HCID 673194195-(4-Iodo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine2×

Product 1

HCID 673186175-Biphenyl-4-yl-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidineYield 77.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an inert gas atmosphere is dissolved 5-(4-iodo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine (compound D1)(0.45 g) and phenylboronic acid (0.35 g) in dimethoxyethane. To this solution are added bis-(triphenylphosphine)-palladium(II) chloride (0.19 mmol) and an aqueous sodium carbonate solution (2M, 6 ml). The reaction mixture is heated to reflux for 4.5 h. After 1 h further phenylboronic acid (0.2 g) is added in order to complete the reaction. The mixture is diluted with ethyl acetate and filtered over silica gel. The product is partitioned between ethyl acetate and an aqueous solution of sodium bicarbonate (5%), the organic phase is dried over sodium sulfate and the crude product is purified by silica gel flash chromatography. A nearly colorless solid (0.3 g) in 50% yield is obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 4.5 h
  3. customthe reaction
  4. filtrationfiltered over silica gel
  5. customThe product is partitioned between ethyl acetate
  6. dry with materialan aqueous solution of sodium bicarbonate (5%), the organic phase is dried over sodium sulfate
  7. customthe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-70998479748949489811774a11e6c067
Source dataset
uspto-grants-2010_06
Patent number
US07745446B2

Reaction notes

Loading…