Triethylamine → 8-fluoro-N-[2-[4-(i-propyl)phenyl]ethyl]-4-quinazolinamine

HRID 35843Notes

Reaction equation

HRID 35843 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=1)([CH3:15])[CH3:14].C(N(CC)CC)C>C(O)C>[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][N:3]=[C:2]2[NH:24][CH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH:13]([CH3:15])[CH3:14])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4100822-(4-(Propan-2-yl)phenyl)ethan-1-amineHCID 199391334-Chloro-8-fluoroquinazoline

Product 1

HCID 199391198-fluoro-N-[2-[4-(i-propyl)phenyl]ethyl]-4-quinazolinamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2 g of 4-chloro-8-fluoroquinazoline, 1.94 g of 2-[4-(i-propyl)phenyl]ethylamine, and 1.21 g of triethylamine in 100 mL of ethanol was heated at reflux for one hour. The ethanol was removed and the remaining product was dissolved in 100 mL of methylenechloride and then washed with aqueous sodium carbonate. The organic layer was then dried and the solvent was removed. The residue was slurried in pentane. Yield: 2.4 g. M.P. 170°-172° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. customThe ethanol was removed
  4. dissolutionthe remaining product was dissolved in 100 mL of methylenechloride
  5. washwashed with aqueous sodium carbonate
  6. customThe organic layer was then dried
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-22ecffae32f44ed6aca698ab258374de
Source dataset
uspto-grants-1995_05
Patent number
US05411963

Reaction notes

Loading…