Ethyl Acetate → HCID 24822776, compound

HRID 2115802Notes

Reaction equation

HRID 2115802 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]2.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:21][C:22]1[N:27]=[C:26](Cl)[CH:25]=[CH:24][N:23]=1.CCOC(C)=O>CS(C)=O>[Cl:21][C:22]1[N:27]=[C:26]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]3)[CH:25]=[CH:24][N:23]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 775312,4-DichloropyrimidineHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 24822776HCID 24822776, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-hydroxy-1-naphthoic acid (10.0 g, 53.1 mmol) in DMSO (60 mL) was added Cs2CO3 (51.9 g, 159.4 mmol). Bubbling was evident. The mixture was stirred at RT for 5 min, at which time 2,4-dichloropyrimidine (15.8 g, 16.3 mmol) was added. The reaction was stirred at RT and monitored by LCMS for the disappearance of starting material. EtOAc (1.0 L) was added, and the reaction was filtered to remove solid Cs2CO3. The mixture was extracted with 2N aqueous NaOH. The aqueous layer was washed with EtOAc, then acidified with 6N aqueous HCl to provide a white suspension. Filtration yielded a white solid.

Workup

  1. customBubbling
  2. additionwas added
  3. filtrationthe reaction was filtered
  4. customto remove solid Cs2CO3
  5. extractionThe mixture was extracted with 2N aqueous NaOH
  6. washThe aqueous layer was washed with EtOAc
  7. customto provide a white suspension
  8. filtrationFiltration
  9. customyielded a white solid

Sources & evidence

ORD record
ord-a34a1585f29e44a8a425bb1f41c083dd
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

Loading…