Ethyl Acetate → HCID 24822776, compound

HRID 1925297Notes

Reaction equation

HRID 1925297 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-1cb34c85f20f41668ddffcbb25ee3c91
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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