Formamidine acetate → HCID 10131272, compound

HRID 2121822Notes

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]=1

Participants

Conditions

Temperature: 162 °C

Procedure

A mixture of 2-fluoro-6-(4-fluorophenoxy)benzonitrile (2.5 g, 11 mmol) and formamidine acetate (Aldrich) (2.3 g, 22 mmol) in 50 ml of N,N-dimethylacetamide was heated at 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 isolated by filtration, washed with water (25 ml), dried and recrystallized from 30 ml of ethanol at 4° C. The precipitate was collected by filtration, washed with ethanol and dried at 50° C. in vacuo to give 4-amino-5-(4-fluorophenoxy)quinazoline (0.3 g, 10.7, m.p. 188-190° C.):

Workup

temperatureAfter cooling to room temperature the reaction mixture
customwas evaporated under reduced pressure
temperatureAfter cooling the suspension overnight
customthe precipitate was isolated by filtration
washwashed with water (25 ml)
customdried
customrecrystallized from 30 ml of ethanol at 4° C
filtrationThe precipitate was collected by filtration
washwashed with ethanol
customdried at 50° C. in vacuo

Sources & evidence

ORD record: ord-c4d0bd45049a43f89c14077fea00afd3
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696482B2

Reaction notes

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