Water → HCID 70020861, compound

HRID 397365Notes

Reaction equation

HRID 397365 reaction equation
CS([C:4]1[N:9]=[C:8]([CH2:10][C:11]2([F:36])[CH:16]=[CH:15][C:14]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:35])([CH2:25][C:26]4[CH:31]=[CH:30][N:29]=[C:28](S(C)=O)[N:27]=4)[CH2:21][CH:20]=3)=[O:18])=[CH:13][CH2:12]2)[CH:7]=[CH:6][N:5]=1)=O.[CH3:37][O-:38].[Na+].O.C1[CH2:45][O:44]CC1>CO>[CH3:37][O:38][C:4]1[N:9]=[C:8]([CH2:10][C:11]2([F:36])[CH:16]=[CH:15][C:14]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:35])([CH2:25][C:26]4[CH:31]=[CH:30][N:29]=[C:28]([O:44][CH3:45])[N:27]=4)[CH2:21][CH:20]=3)=[O:18])=[CH:13][CH2:12]2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 70021249HCID 70021249, compound

Product 1

HCID 70020861HCID 70020861, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2-methylsulfinylpyrimidinyl)methyl-4-fluorophenylketone (5.7 mmol) in 75 mL THF was added 22 mL of 25% NaOMe in MeOH at 0° C. The solution was warmed to room temperature and stirred for 1 h. The solution was then heated at 50° C. for 30 min. Next, the solution was cooled, 200 mL of H2O were added and it was extracted thrice with 100 mL of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give a solid. The solid was then purified by silica gel chromatography with 15-30% ethyl acetate/hexane to give the title compound as a light yellow solid (0.8 g, 57%). ES(+)MS m/e=247 (MH+)

Workup

  1. temperatureThe solution was then heated at 50° C. for 30 min
  2. temperatureNext, the solution was cooled
  3. extractionit was extracted thrice with 100 mL of ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a solid
  8. customThe solid was then purified by silica gel chromatography with 15-30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9f8933e44cf74a29a2a2aaf67f9cb95c
Source dataset
uspto-grants-2003_08
Patent number
US06610695B1

Reaction notes

Loading…