Water → HCID 67282966, compound

HRID 1616177Notes

Reaction equation

HRID 1616177 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12](=[O:23])[NH:13][C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH3:15].[CH:24]([O-])([O-])OCC.O>CN(C=O)C>[O:23]=[C:12]1[C:3]2[C:2](=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)[N:1]=[CH:24][N:13]1[C:14]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 53630039EthylorthoformateHCID 67281942HCID 67281942, compound

Product 1

HCID 67282966HCID 67282966, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of methyl 4-amino-3-[(2-phenylpropan-2-yl)carbamoyl]benzoate (0.13 g, 0.42 mmol) in DMF (2.5 mL) was added ethyl orthoformate (3.0 mL, 18 mmol) followed by one scoop of 3 Å molecular sieves. The reaction mixture was heated to 150° C. and stirred for 1 d. The mixture was cooled to rt, water was added and the mixture was extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes) to afford methyl 4-oxo-3-(2-phenylpropan-2-yl)-3,4-dihydroquinazoline-6-carboxylate (0.11 g, 84%). LC-MS: (FA) ES+ 323.

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionthe mixture was extracted with EtOAc (2×)
  3. washThe combined organic phases were then washed with water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8bc10b9043b84e358c4c31fd9aa7a99d
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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