Sodium hydride → HCID 58574706, compound

HRID 1619294Notes

Reaction equation

HRID 1619294 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:16][CH2:17][CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[N:7]([CH2:16][CH2:17][CH3:18])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 1355556127-Bromo-3,4-dihydroquinazolin-4-one

Product 1

HCID 58574706HCID 58574706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7-bromoquinazolin-4(3H)-one (0.2 g, 0.89 mmol) and DMF (20 mL) was added sodium hydride (85 mg, 3.5 mmol) in portions. The reaction mixture was stirred at room temperature for 15 min. 1-iodopropane (0.18 g, 1.1 mmol) was added dropwise. After stirring for 30 min., the reaction mixture was quenched with water (20 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product. MS (ESI): 267, 269 (MH+).

Workup

  1. stirringAfter stirring for 30 min.
  2. customthe reaction mixture was quenched with water (20 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b8ca9b07a04a4f5484707dc5dfb26521
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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