Potassium Carbonate → HCID 59258890, compound

HRID 2389965Notes

Reaction equation

HRID 2389965 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.[CH3:25][O:26][C:27]1[N:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=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:31]=[N:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[C:18]2=[O:19])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 59258888HCID 59258888, compound

Product 1

HCID 59258890HCID 59258890, compoundYield 44.2%

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-methyl-pyrido[2,3-d]pyrimidin-7(8H)-one (50 mg, 0.126 mmol), 6-methoxypyridin-3-ylboronic acid (21 mg, 0.137 mmol), potassium carbonate (3 M, 0.06 mL) in DMF (1.2 mL) was added dichlorobis(triphenylphosphine)palladium(II) (4.5 mg, 0.0064 mmol). The mixture was degassed with N2, sealed and heated for 30 min at 110° C. The solvent was removed under reduced pressure. The crude mixture was purified by chromatography to give the title compound (23.6 mg, 44%).

Workup

  1. customThe mixture was degassed with N2
  2. customsealed
  3. customThe solvent was removed under reduced pressure
  4. customThe crude mixture was purified by chromatography

Sources & evidence

ORD record
ord-20d040c8f6584fd9a3ec4ba5bc056db3
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

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