Methyl iodide → HCID 17876723, compound

HRID 1377676Notes

Reaction equation

HRID 1377676 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][NH:15][C:14]2=[O:23])[CH2:9][CH2:8]1)=[O:6].I[CH3:31].[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[C:5]([N:7]1[CH2:8][CH2:9][CH:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][N:15]([CH3:31])[C:14]2=[O:23])[CH2:11][CH2:12]1)=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 22914671HCID 22914671, compound

Product 1

HCID 17876723HCID 17876723, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2,4-dimethoxybenzoylpiperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (100 mg, 2.53 mmol) from Example 35 in DMF (50 mL) was added Nail (16 mg of a 60% suspension in mineral oil, 0.40 mmol) followed by iodomethane (0.031 mL, 0.50 mmol). The reaction was stirred for 18 h at ambient temperature. More NaH (10 mg, 0.25 mmol) and iodomethane (0.031 mL, 0.50 mmol) were added and the reaction was stirred at ambient temperature for 24 h. The reaction was quenched by the addition of HOAc (0.2 mL) and the solvents were removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 90:10 EtOAc:hexanes as eluant. The title compound was obtained as an oil (45% yield). TLC: Rf =0.42 (97:3 CHCl3 :MeOH) HPLC (method A): retention time 8.53 min FAB MS: m/z 410 (M+ +H)

Workup

  1. stirringthe reaction was stirred at ambient temperature for 24 h
  2. customThe reaction was quenched by the addition of HOAc (0.2 mL)
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-b65fbca1fd9846c59862ad80fcc4731b
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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