Sodium Carbonate → HCID 178468506, compound

HRID 2390756Notes

Reaction equation

Cl.[CH3:2][NH:3][C:4]([NH2:6])=[NH:5].[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[CH3:16][CH:17]([CH3:26])[C:18](=O)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[F:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]2[N:5]=[C:4]([NH:3][CH3:2])[NH:6][CH:18]([CH:17]([CH3:26])[CH3:16])[C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1-Methylguanidine hydrochloride (8.25 g), 4-Fluorobenzaldehyde (4.2 g), ethyl 4-methyl-3-oxo-pentanoate (5.0 g) and DMF (100 ml) were charged to a vessel equipped with a condenser and connected to a nitrogen line. The resultant mixture stirred until a clear solution is obtained. Sodium carbonate (4.0 g) was charged and the mixture heated to 70° C. for 2 hours. The reaction mixture was cooled to ambient temperature, filtered, and the solvents removed by evaporation under reduced pressure. The resultant oil was triturated in water at 50° C. and cooled to give a slurry that was filtered and dried to give ethyl 4-(4-fluorophenyl)-6-isopropyl-2-methylamino-1,6-dihydropyrimidine-5-carboxylate in 63% yield.

Workup

customequipped with a condenser
customis obtained
temperatureThe reaction mixture was cooled to ambient temperature
filtrationfiltered
customthe solvents removed by evaporation under reduced pressure
customThe resultant oil was triturated in water at 50° C.
temperaturecooled
customto give a slurry that
filtrationwas filtered
customdried

Sources & evidence

ORD record: ord-f18677602af741ca9087a054d25c2590
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273878B2

Reaction notes

Loading…