(+-)-2-Butanol → 6-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16]Cl)[N:9]=[CH:8][NH:7][C:6]2=[O:18].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(O)(CC)C>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[N:9]=[CH:8][NH:7][C:6]2=[O:18]Participants
Conditions
- Temperature
- 105 °C
Procedure
In a 500 mL volume glass vessel equipped with a stirrer, a thermometer and a reflux condenser were placed 95.0 g (0.354 mol) of 6-methoxy-7-(3-chloropropoxy)-quinazolin-4-one, 154.2 g (1.77 mol) of morpholine, and 380 mL of sec-butyl alcohol. The resulting mixture was heated to 105° C. under stirring for 18 hours. After the reaction was complete, 380 mL of methanol was added to the reaction mixture. The resulting mixture was stirred at 70° C. for 30 minutes, and cooled to room temperature. The mixture was then stirred for 30 minutes at room temperature. The precipitated crystalline product was filtered, placed in 190 mL of methanol and stirred for washing, again filtered, and dried at 60° C. under reduced pressure to give 104 g (isolated yield: 92%, purity: 98.81% in terms of area percentage determined by high performance liquid chromatography) of 6-methoxy-7-(3-morpholinopropoxy)quinazolin-4-one as a white crystalline product.
Workup
- customIn a 500 mL volume glass vessel equipped with a stirrer
- stirringThe resulting mixture was stirred at 70° C. for 30 minutes
- temperaturecooled to room temperature
- stirringThe mixture was then stirred for 30 minutes at room temperature
- filtrationThe precipitated crystalline product was filtered
- stirringstirred
- washfor washing
- filtrationagain filtered
- customdried at 60° C. under reduced pressure
Sources & evidence
- ORD record
- ord-84f5e33c73e84a4698b90763171c520f
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367824B2
Reaction notes
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