Morpholine → HCID 67283473, compound

HRID 1616162Notes

Reaction equation

HRID 1616162 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=2)[N:8]=[CH:7]1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:28]1[CH2:29][CH2:30][N:25]([C:2]2[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=2)[CH2:5][N:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=3)[N:8]=[CH:7]2)[CH2:26][CH2:27]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67282590HCID 67282590, compound

Product 1

HCID 67283473HCID 67283473, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial was added ethyl 3-(3-bromobenzyl)-4-oxo-3,4-dihydroquinazoline-6-carboxylate (0.06 g, 0.16 mmol) and morpholine (0.040 mL, 0.47 mmol) in anhydrous 1,4-dioxane (3 mL). The solution was degassed under nitrogen for 10 min then cesium carbonate (0.15 g, 0.46 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.027 g, 0.047 mmol) were added followed by tris(dibenzylideneacetone)dipalladium(0) (0.021 g, 0.023 mmol). The reaction mixture was heated at 120° C. for 30 min in a microwave. The mixture was then concentrated and to the residue was added dichloromethane (3 mL) and water (1 mL). After separation, the aqueous layer was extracted with dichloromethane (3 mL). The combined organic layers were then washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give ethyl 3-(3-morpholinobenzyl)-4-oxo-3,4-dihydroquinazoline-6-carboxylate. LC-MS: (FA) ES+ 394.

Workup

  1. customThe solution was degassed under nitrogen for 10 min
  2. concentrationThe mixture was then concentrated and to the residue
  3. additionwas added dichloromethane (3 mL) and water (1 mL)
  4. customAfter separation
  5. extractionthe aqueous layer was extracted with dichloromethane (3 mL)
  6. washThe combined organic layers were then washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ca70c6c457a94a2c817e8b73538628d3
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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