Sodium Methoxide → HCID 136392063, compound

HRID 2036846Notes

Reaction equation

HRID 2036846 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2([CH3:21])[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15][CH2:14]2)=O)=[CH:8][CH:7]=[CH:6][C:5]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[NH2:2].C[O-].[Na+]>CO>[C:22]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[C:1](=[O:3])[NH:2][C:11]([C:13]2([CH3:21])[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15][CH2:14]2)=[N:10]3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67055921HCID 67055921, compound

Product 1

HCID 136392063HCID 136392063, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution N-(2-carbamoylbiphenyl-3-yl)-2,2,5-trimethyl-1,3-dioxane-5-carboxamide (0.23 g, 0.62 mmol) in methanol was added NaOMe (0.25 mL, 25% in MeOH, 1.2 mmol) and the reaction mixture stirred at 50° C. for 1 h. After this time, the reaction mixture was concentrated and the resulting residue was diluted with ethyl acetate then washed with water. The organic portion was dried and concentrated under reduced pressure to yield a residue. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to yield pure 5-phenyl-2-(2,2,5-trimethyl-1,3-dioxan-5-yl)quinazolin-4(3H)-one (0.2 g, 91% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.49 (br s, 1H), 7.77 (t, 1H, J=8 Hz), 7.64 (d, 1H, J=8 Hz), 7.36-7.28 (m, 5H), 7.21 (d, 1H, J=8 Hz), 4.27 (d, 2H, J=12 Hz), 3.91 (d, 2H, J=12 Hz), 1.40 (s, 3H), 1.35 (d, 6H, 10.2 Hz). LCMS Method W: retention time 2.01 min; [M+1]=351.

Workup

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

Sources & evidence

ORD record
ord-f56afe6b04b0465abecc5fdcacc2fbc5
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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