Methyl iodide → 1,3-Dimethyl-5-nitroquinazoline-2,4(1H,3H)-dione

HRID 552373Notes

Reaction equation

HRID 552373 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=O)[NH:7][C:8](=[O:14])[NH:9]2)([O-:3])=[O:2].[C:16]([O-:19])([O-])=O.[K+].[K+].[CH3:22]I>CN(C=O)C.O>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:16](=[O:19])[N:7]([CH3:6])[C:8](=[O:14])[N:9]2[CH3:22])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 196044425-Nitroquinazoline-2,4(1H,3H)-dione

Product 1

HCID 671658651,3-Dimethyl-5-nitroquinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of Step 1 intermediate (40 g, 193 mmol) in dry DMF (386 ml) was added anhydrous K2CO3 (133.51 g, 966 mmol) and the mixture was stirred at room temperature for 30 min. Methyl iodide (40 ml, 636 mmol) was added slowly with stirring and further stirred at room temperature for 24 h. The reaction mixture was diluted with water (1.5 lit) and the solid precipitated out was filtered, washed with water and dried to give 41 g of the product as yellow solid; 1H NMR (δ ppm, DMSO-d6, 300 MHz): 7.89 (t, J=8.4, 1H); 7.67 (d, J=8.7, 1H); 7.54 (d, J=7.8, 1H); 3.54 (s, 3H); 3.24 (s, 3H). MS (m/z): 236.20 ([M+H]+).

Workup

  1. stirringwith stirring
  2. stirringfurther stirred at room temperature for 24 h
  3. customthe solid precipitated out
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-26ee1481be5b48cfaf97065821df1eb2
Source dataset
uspto-grants-2011_05
Patent number
US07951814B2

Reaction notes

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