Sodium Carbonate → 5-(4'Methoxy-biphenyl-3-yl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine

HRID 19609

Reaction equation

HRID 19609 reaction equation
Br[C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=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>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[N:13]=[C:12]([S:14][CH3:15])[N:11]4[N:16]=[CH:17][CH:18]=[C:10]4[CH:9]=3)[CH:3]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 673192425-(3-Bromo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine2×

Product 1

HCID 673194075-(4'Methoxy-biphenyl-3-yl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidineYield 151.1%

Reagents, catalysts & solvents 3

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

Procedure

Under an inert gas atmosphere is dissolved 5-(3bromophenyl)-7-methylsulfanyl-pyrazolo-[1,5-c]pyrimidine (compound D3)(0.25 g) and 4-methoxyphenyl boronic acid (0.45 g) in dimethoxyethane. To this solution are added bis-(triphenylphosphine)palladium(II) chloride (0.13 mmol) and an aqueous sodium carbonate solution (2M, 8 ml). The reaction mixture is heated to reflux for 18 h 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 dned over sodium sulfate and the crude product is purified by silica gel flash chromatography. A nearly colorless solid (0.41 g) in 60% yield is obtained,

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 18 h The mixture
  3. filtrationfiltered over silica gel
  4. customThe product is partitioned between ethyl acetate
  5. customthe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-b508c1e5041d4659bf7164d867ac64c9
Source dataset
uspto-grants-2010_06
Patent number
US07745446B2

Linked notes

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