Ethyl Acetate → HCID 90020695, compound

HRID 2200095Notes

Reaction equation

HRID 2200095 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.CC([O-])(C)C.[K+].[Cl:15][C:16]1[CH:21]=[C:20](Cl)[N:19]=[CH:18][N:17]=1.CCOC(C)=O>CN(C=O)C.O>[Cl:15][C:16]1[N:17]=[CH:18][N:19]=[C:20]([O:8][C:5]2[N:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 709434,6-DichloropyrimidineHCID 23665647Potassium tert-butoxideHCID 178507770HCID 178507770, compound

Product 1

HCID 90020695HCID 90020695, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Add 5-aminopyridin-2-ol (500 mg, 4.545 mmol), t-BuOK (555 mg, 4.545 mmol) in DMF (20 mL), stir at 25° C. for 30 min. Cool to 0° C., add slowly 4,6-dichloropyrimidine (614 mg, 4.13 mmol). Stir the reaction under N2 for 1 hr. TLC (EtOAc:PE=1:1) shows the reaction is complete. Cool the mixture to 0° C., add water (20 mL), extract with EtOAc (20 mL×2). Combine the organic layers; wash with brine, dry over anhydrous Na2SO4. Filter and concentrate under reduced pressure to give crude product. Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the title compound (650 mg, 70.8%). MS: (M+1): 223.1.

Workup

  1. temperatureCool to 0° C.
  2. stirringStir
  3. customthe reaction under N2 for 1 hr
  4. temperatureCool the mixture to 0° C.
  5. extractionextract with EtOAc (20 mL×2)
  6. washwash with brine
  7. dry with materialdry over anhydrous Na2SO4
  8. filtrationFilter
  9. concentrationconcentrate under reduced pressure
  10. customto give crude product
  11. customPurification by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-4d73a82080ce49a2b261282e0c3d5549
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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