Isopropyl iodide → HCID 23505644, compound

HRID 1993311Notes

Reaction equation

HRID 1993311 reaction equation
[H-].[Na+].[CH2:3]1[CH2:16][O:15][C:14]2[CH:13]=[C:12]3[C:7]([C:8]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:9][C:10](=[O:17])[NH:11]3)=[CH:6][C:5]=2[O:4]1.I[CH:25]([CH3:27])[CH3:26]>CN(C=O)C>[CH2:3]1[CH2:16][O:15][C:14]2[CH:13]=[C:12]3[C:7]([C:8]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:9][C:10]([O:17][CH:25]([CH3:27])[CH3:26])=[N:11]3)=[CH:6][C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 23505670HCID 23505670, compound

Product 1

HCID 23505644HCID 23505644, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% dispersion, 44 mg, 1.07 mmol) in 1 mL of DMF was added a suspension of 6,7-ethylenedioxy-4-phenylquinazolin-2(1H)-one (100 mg, 0.36 mmol) in 4 mL of DMF and stirred at rt for 15 min. 2-Iodopropane (150 μL, 1.45 mmol) was then added and the mixture was heated to ˜60-70° C. for 1.5 h. Excess sodium hydride was quenched with water and the solution extracted with 25 mL of 9:1 EtOAc:hexane. The extract was washed with 2×25 mL water and brine, then dried with MgSO4 and concentrated in vacuo. The crude solid was subjected to flash column chromatography eluting with acetone:hexane to give the title compound 6,7-ethylenedioxy-2-isopropoxy-4-phenylquinazoline (95 mg, 83%). 1H NMR (CDCl3): 7.75 (d, 2H), 7.52 (m, 3H), 7.44 (s, 1H), 7.29 (s, 1H), 5.49 (m, 1H), 4.43-4.30 (m, 4H), 1.46 (d, 6H), followed by the title compound 6,7-ethylenedioxy-1-isopropyl-4-phenylquinazolin-2(1H)-one (9 mg, 8%). 1H NMR (CDCl3): 7.70 (d, 2H), 7.50 (m, 3H), 7.30 (s, 1H), 7.05 (s, 1H), 5.15 (m, 1H), 4.41-4.26 (m, 4H), 1.68 (d, 6H).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated to ˜60-70° C. for 1.5 h
  3. customExcess sodium hydride was quenched with water
  4. extractionthe solution extracted with 25 mL of 9:1 EtOAc
  5. washThe extract was washed with 2×25 mL water and brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated in vacuo
  8. washeluting with acetone

Sources & evidence

ORD record
ord-0bbb12cb1d9a467ab746412ea7799e72
Source dataset
uspto-grants-2010_01
Patent number
US07652006B2

Reaction notes

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