Potassium Carbonate → HCID 178488429, compound

HRID 2390021Notes

Reaction equation

HRID 2390021 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:24])[C:5]2[CH:11]=[C:10](Br)[C:9](=[O:13])[N:8]([C@H:14]3[CH2:19][CH2:18][C@@H:17]([O:20][CH2:21][CH2:22][OH:23])[CH2:16][CH2:15]3)[C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][N:34]=1>[Pd](Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([CH3:24])[C:5]2[CH:11]=[C:10]([C:36]3[CH:35]=[N:34][C:33]([O:32][CH3:31])=[CH:38][CH:37]=3)[C:9](=[O:13])[N:8]([C@H:14]3[CH2:19][CH2:18][C@@H:17]([O:20][CH2:21][CH2:22][OH:23])[CH2:16][CH2:15]3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 178433332HCID 178433332, compound

Product 1

HCID 178488429HCID 178488429, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-6-bromo-8-(cis-4-(2-hydroxyethoxy)cyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (50 mg, 0.13 mmol), potassium carbonate (52 mg, 0.38 mmol), and 2-methoxy-5-pyridine boronic acid (38 mg, 0.25 mmol) in 5:1 dimethylformade:water (1.3 mL) was bubbled with argon for 5 minutes. To the mixture was added bis(tripehnylphosphine) palladium (II) chloride (9 mg, 0.13 mmol) and the microwave vial was immediately sealed and the mixture was bubbled again with argon. After heating for 20 min at 100° C. in the microwave, the mixture was concentrated in vacuo. The residue was dissolved in CHCl3 (60 mL) and washed with water (10 mL) and brine (10 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0-5%) to afford the title compound (50 mg, 93%).

Workup

  1. customwater (1.3 mL) was bubbled with argon for 5 minutes
  2. customthe microwave vial was immediately sealed
  3. customthe mixture was bubbled again with argon
  4. concentrationthe mixture was concentrated in vacuo
  5. dissolutionThe residue was dissolved in CHCl3 (60 mL)
  6. washwashed with water (10 mL) and brine (10 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography
  11. washeluting with chloroform/7 N ammonia in methanol (0-5%)

Sources & evidence

ORD record
ord-3f1e3711cdda49ac8e3435508f2b87f0
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

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