Sodium Methoxide → HCID 136392062, compound

HRID 2036835Notes

Reaction equation

HRID 2036835 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=O)=[CH:8][CH:7]=[CH:6][C:5]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:3])[NH2:2].C[O-].[Na+]>CO>[O:3]=[C:1]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:10]=[C:11]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[NH:2]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67055898HCID 67055898, compound

Product 1

HCID 136392062HCID 136392062, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution tert-butyl 4-(2-carbamoylbiphenyl-3-ylcarbamoyl)piperidine-1-carboxylate (1.0 g, 2.4 mmol) in methanol was added NaOMe (2.6 mL, 25% in MeOH, 12.3 mmol). The resulting reaction mixture was stirred at RT for 14 h. After this time, the reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate and then washed with water. The organic portion was dried, concentrated under reduced pressure to yield a residue. The residue was purified by ISCO chromatography (30% EtOAc in hexanes) to yield tert-butyl 4-(4-oxo-5-phenyl-3,4-dihydroquinazolin-2-yl)piperidine-1-carboxylate (0.60 g, 67% yield) as a white solid. LCMS Method W: retention time 2.07 min; [M+1]=422.2.

Workup

  1. customThe resulting reaction mixture
  2. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure
  3. additionthe resulting residue was diluted with ethyl acetate
  4. washwashed with water
  5. customThe organic portion was dried
  6. concentrationconcentrated under reduced pressure
  7. customto yield a residue
  8. customThe residue was purified by ISCO chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8b590f00016e49f484483223a5584259
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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