Water → HCID 57654506, compound

HRID 1661819Notes

Reaction equation

HRID 1661819 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[N:6][C:5]2=[O:12].[H-].[Na+].Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.O>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:5]2=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 178518218HCID 178518218, compound

Product 1

HCID 57654506HCID 57654506, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Iodo-1H-quinazolin-4-one (0.50 g, 1.84 mmol) was added to a solution of sodium hydride (0.110 g, 2.76 mmol) in THF (10 mL) and stirred at room temperature for one hour. 1-Chloromethyl-4-methoxy-benzene (0.345 g, 2.21 mmol) was added and the reaction was stirred for several hours. Water was added and the crude product was extracted from ethyl acetate and evaporated in vacuo. The product was purified via silica gel column chromatography in hexane:ethyl acetate (4:1) to give 0.69 g (96%) of 6-iodo-3-(4-methoxy-benzyl)-3H-quinazolin-4-one. 1H NMR (400 MHz, CDCl3) δ 8.57 (d, 1H, J=2.0 Hz), 8.01 (s, 1H), 7.90 (dd, 1H, J=2.0, 8.8 Hz), 7.33 (d, 1H, J=8.8 Hz), 7.22 (d, 2H, J=8.0 Hz), 6.80 (d, 2H, J=8.8 Hz), 5.03 (s, 2H), 3.70 (s, 3H).

Workup

  1. stirringthe reaction was stirred for several hours
  2. extractionthe crude product was extracted from ethyl acetate
  3. customevaporated in vacuo
  4. customThe product was purified via silica gel column chromatography in hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-36017e63e8804d858858db8d9a5bc3bd
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

Loading…