Phenol → 4-Amino-5-Fluoroquinazoline

HRID 1067484Notes

Reaction equation

HRID 1067484 reaction equation
C1(O)C=CC=CC=1.CC(C)([O-])C.[K+].N[C:15]1[N:24]=[C:23]([NH2:25])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[F:26])[N:16]=1>CS(C)=O.O>[NH2:25][C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[F:26])[N:16]=[CH:15][N:24]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 4562462,4-Quinazolinediamine, 5-fluoro-HCID 23665647Potassium tert-butoxide

Product 1

HCID 7153314-Amino-5-Fluoroquinazoline

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A solution of phenol (optionally substituted) in dimethyl suiphoxide was added to a stirred mixture of potassium tert-butoxide in dimethyl suiphoxide at room temperature. After 15 minutes 2,4-diamino-5-fluoroquinazoline was added all at once (as the solid) and the mixture was heated to ca 50° C. for 7 hours. After cooling to room temperature the suspension was diluted with water, the solid collected by is filtration, washed, recrystallized from ethanol or n-butyl acetate and dried at 50° C. in vacuo. In particular, 4-Amino-5-fluoroquinazoline was prepared from 2,6-difluorobenzonitrile (Lancaster, Acros) according to the published method (J. Heterocyclic. Chem. 28, 1357 (1991)).

Workup

  1. temperaturewas heated to ca 50° C. for 7 hours
  2. customthe solid collected
  3. filtrationfiltration
  4. washwashed
  5. customrecrystallized from ethanol or n-butyl acetate
  6. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-318c894060bc45c888f935d205ca5919
Source dataset
uspto-grants-2001_06
Patent number
US06248771B1

Reaction notes

Loading…