Dimethyl Sulfate → HCID 19863331, compound

HRID 1761853Notes

Reaction equation

HRID 1761853 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].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 6497Dimethyl SulfateHCID 19863329HCID 19863329, 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 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 which 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 which

Sources & evidence

ORD record
ord-9e526ad42d874bf29700d8cdb9396c9f
Source dataset
uspto-grants-1989_05
Patent number
US04829066

Reaction notes

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