Tetrahydrofuran → HCID 19354338, compound

HRID 1930764Notes

Reaction equation

HRID 1930764 reaction equation
[C:1]([C:5]1[O:6][C:7](=[O:15])[C:8]2[CH:14]=[CH:13][CH:12]=[N:11][C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].O1CCC[CH2:17]1.C[Mg]Br.[Cl-].[NH4+]>O>[C:7]([C:8]1[C:9]([NH:10][C:5](=[O:6])[C:1]([CH3:4])([CH3:3])[CH3:2])=[N:11][CH:12]=[CH:13][CH:14]=1)(=[O:15])[CH3:17]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 57867428HCID 57867428, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19354338HCID 19354338, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

To a mixture of 2-tert-butyl-4H-pyrido[2,3-d][1,3]oxazin-4-one (10.2 g, 50 mmol) and tetrahydrofuran (50 mL) was added methyl magnesium bromide (0.97M tetrahydrofuran solution, 100 mL, 97 mmol) dropwise at −78° C., after the dropwise addition was finished, which was stirred at −78° C. for 30 minutes. To the reaction mixture were added a saturated aqueous solution of ammonium chloride and water, which was extracted with ethyl acetate, and the organic layer was washed with an aqueous solution of ammonium chloride. The solvent was evaporated under a reduced pressure and the precipitated solid was filtered to obtain the title compound (9.1 g).

Workup

  1. additionafter the dropwise addition
  2. extractionwas extracted with ethyl acetate
  3. washthe organic layer was washed with an aqueous solution of ammonium chloride
  4. customThe solvent was evaporated under a reduced pressure
  5. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-29d51df788024a41bdc6e45fced57b06
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

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