HCID 19735135, compound → HCID 135749786, compound

HRID 326586Notes

Reaction equation

HRID 326586 reaction equation
O.O.O.[F-].[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH3:17])([CH3:16])[N:13]=[C:12]([C:18]3[C:23]([O:24]COCC[Si](C)(C)C)=[C:22]([Si](C)(C)C)[CH:21]=[CH:20][N:19]=3)[C:11]=2[CH:37]=1)#[N:6]>O1CCCC1>[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH3:17])([CH3:16])[N:13]=[C:12]([C:18]3[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][N:19]=3)[C:11]=2[CH:37]=1)#[N:6]

Participants

4

Reactant 2

HCID 19735135HCID 19735135, compoundHCID 22448177HCID 22448177, compound

Product 1

HCID 135749786HCID 135749786, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Molecular sieves 5A (5 g) and tertrabutylammonium fluoride trihydrate (3.2 g) were added to a solution of 6-cyano-2,2-dimethyl-4-[4-trimethylsilyl-3-(2-trimethylsilylethoxymethyloxy)pyridin-2-yl]-2H-1,3-benzoxazine (2.5 g) in tetrahydrofuran (20 ml), and the mixture was heated under reflux for 30 minutes. After air-cooling, the mixture was extracted by addition of ethyl acetate. The organic layer was washed with saturated saline solution, the solvent was distilled off under reduced pressure and the residue was crystallized from ethyl acetate to obtain 6-cyano-2,2-dimethyl-4-(3-hydroxypyridin-2-yl)-2H-1,3-benzoxazine (0.19 g) (Compound 12).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter air-cooling
  4. extractionthe mixture was extracted by addition of ethyl acetate
  5. washThe organic layer was washed with saturated saline solution
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9dcc5de7434c46be829620175f4055e3
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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