Methyl iodide → 6-(4-Methoxydibenzo[b,d]furan-1-yl)-3-methyl-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

HRID 2383982Notes

Reaction equation

HRID 2383982 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2([C:27]#[N:28])[CH2:25][CH2:24][C:23]3[N:22]=[CH:21][NH:20][C:19](=[O:26])[C:18]=3[CH2:17]2)=[CH:5][CH:4]=1.[C:29](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2([C:27]#[N:28])[CH2:25][CH2:24][C:23]3[N:22]=[CH:21][N:20]([CH3:29])[C:19](=[O:26])[C:18]=3[CH2:17]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 1356204896-(4-Methoxydibenzo[b,d]furan-1-yl)-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

Product 1

HCID 248044526-(4-Methoxydibenzo[b,d]furan-1-yl)-3-methyl-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrileYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a well stirred slurry of compound obtained in example 13 (75 mg, 0.2 mmol) and cesium carbonate (73 mg, 0.22 mmol) in dry DMF (5 ml) was added iodomethane (36.92 mg, 0.26 mol) and the mixture was allowed to stir for 1 hr at room temperature under nitrogen atmosphere. The reaction mixture was quenched with ice water (50 ml), and then extracted with ethyl acetate (50 ml). The organic layer was washed with water followed by brine and dried over sodium sulfate. The organic layer was concentrated under vacuum and the crude product was purified by column chromatography to get 40 mg of the pure product (Yields-52%) MP-235.4-240.8° C.

Workup

  1. customThe reaction mixture was quenched with ice water (50 ml)
  2. extractionextracted with ethyl acetate (50 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationThe organic layer was concentrated under vacuum
  6. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-33be2c9f1b5749918a0a4c50384c2106
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

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