Potassium Carbonate → HCID 59258830, compound

HRID 641642Notes

Reaction equation

HRID 641642 reaction equation
Br[C:2]1[C:18](=[O:19])[N:17]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:5]2[N:6]=[C:7]([NH:11][CH2:12][C:13]([OH:16])([CH3:15])[CH3:14])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.[OH:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=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>[CH:20]1([N:17]2[C:5]3[N:6]=[C:7]([NH:11][CH2:12][C:13]([OH:16])([CH3:15])[CH3:14])[N:8]=[C:9]([CH3:10])[C:4]=3[CH:3]=[C:2]([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([OH:25])[CH:31]=3)[C:18]2=[O:19])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 59258888HCID 59258888, compound

Product 1

HCID 59258830HCID 59258830, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-8-cyclopentyl-2-(2-hydroxy-2-methylpropylamino)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (52.5 mg, 0.133 mmol), 3-hydroxyphenylboronic acid (20.5 mg, 0.149 mmol), potassium carbonate (3 M, 0.06 mL) in DMF (1.2 mL) was added dichlorobis(triphenylphosphine)palladium(II) (5 mg, 0.007 mmol). The mixture was degassed with N2, sealed and heated for 30 min at 110° C. The mixture was poured into brine and extracted with EtOAc. The EtOAc layer was dried (anhydrous sodium sulfate), filtered, and concentrated under reduced pressure. The crude product was purified by chromatography to give the title compound (12 mg, 22%).

Workup

  1. customThe mixture was degassed with N2
  2. customsealed
  3. additionThe mixture was poured into brine
  4. extractionextracted with EtOAc
  5. dry with materialThe EtOAc layer was dried (anhydrous sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-83d6e506ba084bbd8b7755e66d4bd5c1
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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