Potassium Phosphate, Tribasic → HCID 58269022, compound

HRID 1428188Notes

Reaction equation

HRID 1428188 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[N:14][C:13]=23)O1.[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:19][C:20]1[N:21]=[CH:22][N:23]=[C:24]([C:9]2[CH:10]=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[N:14][C:13]=23)[CH:25]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 709434,6-DichloropyrimidineHCID 75806TricyclohexylphosphineHCID 58268917Pyrazolo[1,5-a]pyrimidine-3-boronic acid pinacol ester

Product 1

HCID 58269022HCID 58269022, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of compound 13g (14.3 mmol) in DMF (90 mL), was added 4,6-dichloropyrimidine (14.3 mmol), K3PO4, (42.7 mmol) and PCy3 (1.4 mmol) at rt. The mixture was purged with Ar for 45 min, Pd2(dba)3 (0.70 mmol) added and again the mixture purged with Ar for 30 min and heated to 100° C. for 1 h. The reaction was cooled to rt, EtOAc (800 mL) added, and the mixture filtered through Celite®. The combined filtrate was washed with water (3×200 mL), 2N aq. HCl solution (400 mL), sat. aq. NaHCO3 and brine solution (200 mL). The organic layer was dried (Na2SO4), filtered and concentrated to give a crude compound as a brown residue. The crude compound 7f was purified by column chromatography (100-200 mesh silica gel, 0-70% EtOAc/Petroleum ether). The product was obtained as a solid (350 mg, 10.6%). TLC system: EtOAc: Pet ether (7:3). Rf value: 0.56. mp: 260-270° C.

Workup

  1. customThe mixture was purged with Ar for 45 min
  2. customagain the mixture purged with Ar for 30 min
  3. temperatureThe reaction was cooled to rt
  4. additionEtOAc (800 mL) added
  5. filtrationthe mixture filtered through Celite®
  6. washThe combined filtrate was washed with water (3×200 mL), 2N aq. HCl solution (400 mL), sat. aq. NaHCO3 and brine solution (200 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a crude compound as a brown residue
  11. customThe crude compound 7f was purified by column chromatography (100-200 mesh silica gel, 0-70% EtOAc/Petroleum ether)

Sources & evidence

ORD record
ord-f9b0cb66bc0844dfa951af1e56ddbc70
Source dataset
uspto-grants-2015_01
Patent number
US08937064B2

Reaction notes

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