Methyl iodide → 6-Iodo-3-methyl-3H-quinazolin-4-one

HRID 2221142Notes

Reaction equation

HRID 2221142 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][NH:8][C:7]2=[O:14].I[CH3:16]>CN(C=O)C.C(Cl)(Cl)Cl.C(O)(C)C>[I:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]([CH3:16])[C:7]2=[O:14]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1354016666-Iodoquinazolin-4-one

Product 1

HCID 171390916-Iodo-3-methyl-3H-quinazolin-4-oneYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Suspend sodium hydride (1.13 g, 47 mmol) in a solution of 6-iodo-3H-quinazolin-4-one (2.5 g, 9.2 mmol) in DMF. Stir at room temperature for 20 min, add iodomethane (6.6 g, 46 mmol) into the mixture and stir for 2 h. Dilute the mixture with 3:1 chloroform/isopropyl alcohol and wash with saturated sodium chloride solution. Dry the organic phase (sodium sulfate) and concentrate in vacuo. Purify the residue with flash chromatography (dichloromethane to dichloromethane/methanol) to give 2.5 g (95%) of the titled compound as a white solid. MS ES+ m/e 287 (M+1).

Workup

  1. stirringstir for 2 h
  2. washwash with saturated sodium chloride solution
  3. dry with materialDry the organic phase (sodium sulfate)
  4. concentrationconcentrate in vacuo
  5. customPurify the residue with flash chromatography (dichloromethane to dichloromethane/methanol)

Sources & evidence

ORD record
ord-a95ffa6bc9e64b9a95750d43f1b9f424
Source dataset
uspto-grants-2008_05
Patent number
US07368445B2

Reaction notes

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