HCID 19863329, compound → HCID 19863331, compound

HRID 1164792Notes

Reaction equation

HRID 1164792 reaction equation
[CH3:1][Sn:2]([CH3:15])([CH3:14])[C:3]1[CH:12]=[N:11][C:10]2[NH:9][C:8](=[O:13])[CH2:7][O:6][C:5]=2[CH:4]=1.[Li]N([Si](C)(C)C)[Si](C)(C)[CH3:19].S(O)(O)(=O)=O.COS(OC)(=O)=O>C1COCC1>[CH3:19][N:9]1[C:8](=[O:13])[CH2:7][O:6][C:5]2[CH:4]=[C:3]([Sn:2]([CH3:15])([CH3:14])[CH3:1])[CH:12]=[N:11][C:10]1=2

Participants

5

Reactant 3

HCID 19863329HCID 19863329, compoundHCID 86743782HCID 86743782, compoundHCID 178418261HCID 178418261, compound

Product 1

HCID 19863331HCID 19863331, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 680 mg of 7-trimethylstannyl-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (0.0022 mole) in 10 ml of THF is added 2.4 ml of LiN(TMS)2 (0.0024 mole) in THF. The homogenous solution is maintained under nitrogen at room temperature for 20 min , 300 mg (0.0024 mole) of dimethylsulfate sulfate is added and the reaction mixture allowed to stir overnight. The reaction mixture is then quenched with 10 ml of sat. ammonium chloride and extracted with 3×50 ml ethyl acetate. The ethyl acetate is then washed with 3×10 ml sat. ammonium chloride, dried over sodium sulfate and concentrated to obtain off white product whish is used directly in the next step.

Workup

  1. customThe reaction mixture is then quenched with 10 ml of sat. ammonium chloride
  2. extractionextracted with 3×50 ml ethyl acetate
  3. washThe ethyl acetate is then washed with 3×10 ml sat. ammonium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto obtain off white product whish

Sources & evidence

ORD record
ord-01136c9591994b6281234cb09d80eb0b
Source dataset
uspto-grants-1990_03
Patent number
US04906629

Reaction notes

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