Guanidine Hydrochloride → HCID 178496922, compound

HRID 2390753Notes

Reaction equation

Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[CH3:15][CH:16]([CH3:24])[C:17](=O)[CH2:18][C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:4][C:3]1[NH:5][CH:17]([CH:16]([CH3:24])[CH3:15])[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:11]([C:10]2[CH:13]=[CH:14][C:7]([F:6])=[CH:8][CH:9]=2)[N:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Guanidine hydrochloride (12.1 g), 4-Fluorobenzaldehyde (7.0 g), methyl 4-methyl-3-oxo-pentanoate (8.9 g) and DMF (150 ml) were charged to a vessel equipped with a condenser and connected to a nitrogen line. The resultant mixture was stirred until a clear solution was obtained. Potassium carbonate (17.5 g) is charged and the mixture heated to 70° C. for 3 hours. The reaction mixture was cooled to ambient temperature and filtered. It contained methyl 2-amino-4-(4-fluorophenyl)-6-isopropyl-1,6-dihydropyrimidine-5-carboxylate in 55% yield. An analytical sample was prepared by removing the reaction solvents by evaporation under reduced pressure, precipitating the product from the resultant oil in acetonitrile and recrystallisation from acetonitrile.

Workup

customequipped with a condenser
customwas obtained
temperatureThe reaction mixture was cooled to ambient temperature
filtrationfiltered
customAn analytical sample was prepared
customby removing the reaction solvents
customby evaporation under reduced pressure
customprecipitating the product from the resultant oil in acetonitrile
customrecrystallisation from acetonitrile

Sources & evidence

ORD record: ord-f5efb924c67643b18d9aa0db5e519ad2
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273878B2

Reaction notes

Loading…