Potassium Carbonate → HCID 73332620, compound

HRID 2203258Notes

Reaction equation

HRID 2203258 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.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[CH:38][C:39]([NH2:42])=[N:40][CH:41]=2)O1.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>[NH2:42][C:39]1[N:40]=[CH:41][C:36]([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:37][CH:38]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 90077584HCID 90077584, compound

Product 1

HCID 73332620HCID 73332620, compoundYield 12.4%

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 (400 mg, 1 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (440 mg, 2.0 mmol), potassium carbonate (414 mg, 3.0 mmol) and tetrakis(triphenylphosphine)palladium(58 mg, 0.05 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, concentrated, and separated by silicagel column chromatography (EtOAc/PE=0-10/1) to obtain a crude product, which was washed with methanol to obtain a yellow solid of 9-(6-aminopyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)pyrimidino[5,4-c][1,5]naphthyridine-2,4(1H,3H)-dione (56 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. customseparated by silicagel column chromatography (EtOAc/PE=0-10/1)
  6. customto obtain a crude product, which
  7. washwas washed with methanol

Sources & evidence

ORD record
ord-d7ec33c2c7904212b401ac74ccc415b9
Source dataset
uspto-grants-2016_06
Patent number
US09365572B2

Reaction notes

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