Dimethylcarbamoyl Chloride → 2-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N,N-dimethylacetamide

HRID 547453

Reaction equation

HRID 547453 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:31][N:32]([CH3:36])[C:33](Cl)=[O:34]>O1CCCC1>[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH2:20][C:33]([N:32]([CH3:36])[CH3:31])=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 583781963-benzyl-7-chloro-2-methylquinazolin-4(3H)-one

Product 1

HCID 583781752-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N,N-dimethylacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Benzyl-7-chloro-2-methylquinazolin-4 (3H)-one (2 g, 1 eq.) was dissolved in tetrahydrofuran (20 ml). The solution was cooled to −78° C. for 15 minutes. Lithium hexamethyl disilazide (LHMDS) was added slowly and the mixture was stirred at −78° C. for 45 minutes. Dimethylcarbamyl chloride was added and the mixture was stirred at −78° C. for 1 h. The reaction was allowed to warm to room temperature and stirred for 3 h. The solvent was evaporated and the resulting solid was dissolved in ethyl acetate. The ethyl acetate layer was washed with water, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to give 2-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N,N-dimethylacetamide (1.2 g) as a solid.

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 h
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 h
  4. customThe solvent was evaporated
  5. dissolutionthe resulting solid was dissolved in ethyl acetate
  6. washThe ethyl acetate layer was washed with water, saturated sodium bicarbonate, saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-05603e43da654f5c8e17e84f8dc2034e
Source dataset
uspto-grants-2011_05
Patent number
US07939539B2

Linked notes

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