Potassium Carbonate → HCID 73438318, compound

HRID 2203259Notes

Reaction equation

HRID 2203259 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[C:12](=[O:27])[NH:13][C:14](=[O:26])[N:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=4)[C:5]=3[C:4]=2[N:3]=1.[CH3:28][O:29][C:30]1[N:35]=[CH:34][C:33](OB(O)O)=[CH:32][N:31]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:28][O:29][C:30]1[N:35]=[CH:34][C:33]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[C:12](=[O:27])[NH:13][C:14](=[O:26])[N:15]([C:16]5[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=5)[C:5]=4[C:4]=3[N:3]=2)=[CH:32][N:31]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 86714231HCID 86714231, compoundHCID 90077584HCID 90077584, compound

Product 1

HCID 73438318HCID 73438318, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

9-chloro-1-(3-(trifluoromethyl)phenyl)pyrimidino[5,4-c][1,5]naphthyridine-2,4(1H,3H)-dione (300 mg, 0.77 mmol), (2-methoxypyrimidin-5-yl)boric acid (119 mg, 0.77 mmol), potassium carbonate (317 mg, 2.3 mmol) and tetrakis(triphenylphosphine)palladium(45 mg, 0.04 mmol) were added to 40 mL dioxane and 2 mL water. The resulting mixture was reacted under reflux in the nitrogen protection for 18 hrs, cooled to room temperature, filtered with Celite, and concentrated. 40 mL water was added. The resulting mixture was filtered to obtain a crude product, which was successively washed with ethyl acetate (30 mL) and methanol (10 mL) to produce 9-(2-methoxypyrimidin-5-yl)-1-(3-(trifluoromethyl)phenyl)pyrimidino[5,4-c][1,5]naphthyridine-2,4(1H,3H)-dione (150 mg).

Workup

  1. customThe resulting mixture was reacted
  2. temperatureunder reflux in the nitrogen protection for 18 hrs
  3. filtrationfiltered with Celite
  4. concentrationconcentrated
  5. addition40 mL water was added
  6. filtrationThe resulting mixture was filtered
  7. customto obtain a crude product, which
  8. washwas successively washed with ethyl acetate (30 mL) and methanol (10 mL)

Sources & evidence

ORD record
ord-168a50220b004c69be8e6031246bfdee
Source dataset
uspto-grants-2016_06
Patent number
US09365572B2

Reaction notes

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