Ethanol → HCID 46203130, compound

HRID 1914775Notes

Reaction equation

HRID 1914775 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[CH:16][CH:15]=2)[C:10]([F:13])([F:12])[F:11])[N:5]=[C:4]([NH2:27])[N:3]=1.[O:28]=[C:29]([NH:34][C:35]1[CH:40]=[CH:39][C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31].C([O-])([O-])=O.[Na+].[Na+].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.O>[NH2:27][C:4]1[N:3]=[C:2]([C:38]2[CH:37]=[CH:36][C:35]([NH:34][C:29](=[O:28])[C:30]([O:32][CH3:33])=[O:31])=[CH:40][CH:39]=2)[CH:7]=[C:6]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[CH:16][CH:15]=2)[C:10]([F:13])([F:12])[F:11])[N:5]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 585161494-Chloro-6-(2,2,2-trifluoro-1-(3'-fluorobiphenyl-4-yl)ethoxy)pyrimidin-2-amineHCID 58516151HCID 58516151, compound

Product 1

HCID 46203130HCID 46203130, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

4-chloro-6-(2,2,2-trifluoro-1-(3′-fluorobiphenyl-4-yl)ethoxy)pyrimidin-2-amine (320 mg, 0.806 mmol), methyl 2-oxo-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)acetate (320 mg, 0.95 mmol), dichlorobis(triphenylphosphine)palladium (79 mg, 0.11 mmol), and Na2CO3 (212 mg, 2.0 mmol) were added to a mixture of ethanol (10 mL) and water (10 mL) in a round-bottom flask. The flask was heated to reflux for 8 hours. The reaction mixture was cooled and solvent was removed. The residue was dissolved in 10 mL of 0.5 M NaOH solution, filtered, and the filtration was extracted with EtOAc. The organic portion was dried and the solvent was removed to get 250 mg of the above-named compound. 1H NMR (300 MHz, CD3OD): δ δ 7.90 (m, 2H), 7.77 (s, 3H), 7.60 (m, 2H), 7.44 (m, 2H), 7.22 (m, 1H), 7.10 (m, 1H), 7.05 (s, 1H), 6.83 (m, 1H), 5.09 (m, 1H), 3.67 (s, 3H); M+1=541.

Workup

  1. temperatureThe flask was heated
  2. temperatureto reflux for 8 hours
  3. temperatureThe reaction mixture was cooled
  4. customsolvent was removed
  5. dissolutionThe residue was dissolved in 10 mL of 0.5 M NaOH solution
  6. filtrationfiltered
  7. filtrationthe filtration
  8. extractionwas extracted with EtOAc
  9. customThe organic portion was dried
  10. customthe solvent was removed

Sources & evidence

ORD record
ord-e172c693378848d6a15943c6b11d17bf
Source dataset
uspto-grants-2013_12
Patent number
US08614222B2

Reaction notes

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