Sodium Methoxide → HCID 136348036, compound

HRID 591594Notes

Reaction equation

HRID 591594 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][C:12](F)=[CH:13][C:14]=3[O:19][CH2:20][CH2:21][O:22][CH:23]([CH3:25])[CH3:24])[N:9]=2)[CH:5]=[C:4]([CH3:27])[N:3]=1.[CH3:28][O-:29].[Na+]>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][C:12]([O:29][CH3:28])=[CH:13][C:14]=3[O:19][CH2:20][CH2:21][O:22][CH:23]([CH3:25])[CH3:24])[N:9]=2)[CH:5]=[C:4]([CH3:27])[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 136348061HCID 136348061, compound

Product 1

HCID 136348036HCID 136348036, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-(2,6-Dimethyl-pyridin-4-yl)-7-fluoro-5-(2-isopropoxy-ethoxy)-3H-quinazolin-4-one (22) (960 mg, 2.58 mmol) was taken up in anhydrous DMF (10 mL). Sodium methoxide (25% solution in methanol, 12.9 mmol) was added. After the addition, the reaction mixture was stirred at 60° C. for 72 hours. The reaction mixture was cooled to room temperature, and quenched with saturated solution of NH4Cl. The product was extracted with ethyl acetate (3×200 mL). The combined organic layer was washed with water, brine, dried over Na2SO4, and evaporated to give crude product. The crude compound was purified by preparative HPLC, to give the title compound 23 as a white solid.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with saturated solution of NH4Cl
  4. extractionThe product was extracted with ethyl acetate (3×200 mL)
  5. washThe combined organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto give crude product
  9. customThe crude compound was purified by preparative HPLC

Sources & evidence

ORD record
ord-de08ffdd44db4c609f43778ff524d280
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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