Ethanol → HCID 24958428, compound

HRID 1187269Notes

Reaction equation

HRID 1187269 reaction equation
[H-].[Na+].Cl[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:12]=2)[N:7]=[CH:6][N:5]=1.[CH2:21]([OH:23])[CH3:22]>>[CH2:21]([O:23][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:12]=2)[N:7]=[CH:6][N:5]=1)[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 57958802HCID 57958802, compound

Product 1

HCID 24958428HCID 24958428, compoundYield 88%

Procedure

To absolute ethanol (10 ml) was added NaH (80 mg of a 60% dispersion in mineral oil, 2.0 mmol). The mixture was stirred at room temperature for 10 minutes. Then, 4-chloro-6-(4-fluorophenyl)-quinazoline (52 mg, 0.2 mmol) was added to this solution. The resulting mixture was stirred at room temperature for another 30 minutes. The solvents were evaporated in vacuo and the crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of ethanol and dichloromethane in a volume ratio of 1:100), yielding the title compound as a white solid (46 mg, yield: 88%) was characterized by its mass spectrum as follows: MS (m/z): 269 ([M+H]+, 100).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for another 30 minutes
  2. customThe solvents were evaporated in vacuo
  3. customthe crude residue was purified by silica gel flash chromatography
  4. additiona mixture of ethanol and dichloromethane in a volume ratio of 1:100),

Sources & evidence

ORD record
ord-536b4ad8e55d47d7a4be4d83816d5379
Source dataset
uspto-grants-2014_03
Patent number
US08673929B2

Reaction notes

Loading…