Formamidine acetate → HCID 10131272, compound
Reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:3]=1[C:4]#[N:5].C(O)(=O)C.[CH:22]([NH2:24])=[NH:23]>CN(C)C(=O)C>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[CH:7][C:6]=2[O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:24]=[CH:22][N:23]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 162 °C
Procedure
A mixture of 2-fluoro-6-(4-fluorophenoxy) benzonitrile (2.5 g, 11 mmol, Maybridge) and formamidine acetate (2.3 g, 22 mmol, Aldrich) in 50 mL of N,N-dimethylacetamide was heated to 162° C. under nitrogen for 9 hours. After cooling to room temperature the reaction mixture was evaporated under reduced pressure. The product was suspended in 80 mL of cold water and the pH adjusted to 8.5 with concentrated ammonium hydroxide. After cooling the suspension overnight, the precipitate was collected by vacuum filtration, washed with water (25 mL), dried and recrystallized from 30 mL of ethanol at 4° C. The precipitate was collected by vacuum filtration, washed with ethanol, and dried at 50° C. to give 0.3 g (10.7% yield) of 4-amino-5-(4-fluorophenoxy)quinazoline, M.P. 188-190° C.
Workup
- temperatureAfter cooling to room temperature the reaction mixture
- customwas evaporated under reduced pressure
- temperatureAfter cooling the suspension overnight
- filtrationthe precipitate was collected by vacuum filtration
- washwashed with water (25 mL)
- customdried
- customrecrystallized from 30 mL of ethanol at 4° C
- filtrationThe precipitate was collected by vacuum filtration
- washwashed with ethanol
- customdried at 50° C.
Sources & evidence
- ORD record
- ord-52a79fe7ff404ed3bd592785e0ec476a
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06204267B1
Reaction notes
Loading…