Potassium Carbonate → HCID 136037979, compound

HRID 555515Notes

Reaction equation

HRID 555515 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:29])[NH:6][C:7]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([CH2:24][O:25]C(=O)C)=[O:23])=[CH:17][CH:16]=1)=[N:8]2.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:29])[NH:6][C:7]([C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:23])[CH2:24][OH:25])=[CH:19][CH:20]=1)=[N:8]2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 136398856HCID 136398856, compound

Product 1

HCID 136037979HCID 136037979, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The yellow solid was triturated with ether and methanol to provide acetic acid [4-(5,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenylcarbamoyl]-methyl ester (112 mg, 37%). To a solution of acetic acid [4-(5,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenylcarbamoyl]-methyl ester (0.23 g, 0.59 mmol) in THF/methanol mixture (3.5 mL/3.5 mL) was added potassium carbonate (0.41 g, 2.95 mmol). The reaction mixture was heated at reflux overnight and the solvent was concentrated under vacuum and diluted with water (60 mL) to obtain a precipitate. The yellow solid was filtered, washed with water (20 mL), methanol and dried under vacuum to provide crude compound. The yellow solid was triturated with ether and methanol to provide the desired compound N-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)phenyl)-2-hydroxyacetamide (55 mg, 55%). Selected data: MS (ES) m/z: 356.1; mp 318-319° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationthe solvent was concentrated under vacuum
  4. additiondiluted with water (60 mL)
  5. customto obtain a precipitate
  6. filtrationThe yellow solid was filtered
  7. washwashed with water (20 mL), methanol
  8. customdried under vacuum
  9. customto provide crude compound
  10. customThe yellow solid was triturated with ether and methanol

Sources & evidence

ORD record
ord-c9263984cde8433abf8f67fdf46e8206
Source dataset
uspto-grants-2011_11
Patent number
US08053440B2

Reaction notes

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