HCID 19780822, compound → HCID 19780831, compound

HRID 2081142Notes

Reaction equation

Cl[C:2]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([CH3:26])[N:21]([CH3:27])[C:20]2=[O:28])=[CH:14][C:3]=1[C:4]([O:6][C:7]([C:10]([O:12][CH3:13])=[O:11])([CH3:9])[CH3:8])=[O:5].[Cu][C:30]#[N:31]>CN1CCCN(C)C1=O>[C:30]([C:2]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([CH3:26])[N:21]([CH3:27])[C:20]2=[O:28])=[CH:14][C:3]=1[C:4]([O:6][C:7]([C:10]([O:12][CH3:13])=[O:11])([CH3:9])[CH3:8])=[O:5])#[N:31]

Participants

Conditions

Temperature: 220 °C

Procedure

A mixture of 1.5 g of 1-methoxycarbonyl-1-methylethyl 2-chloro-5-[3,6-dihydro-3 4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-4-fluorobenzoate and 0.4 g of copper(I) cyanide in 20 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is heated to 220° C. under nitrogen for 6 hours. After cooling to room temperature the mixture is filtered and the filtrate is dissolved in 200 ml of ethyl acetate. The solution is washed four times with 50 ml of water each time, the combined organic phases are dried and concentrated under reduced pressure. In this manner there is obtained 1-methoxycarbonyl-1-methylethyl 2-cyano-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-4-fluorobenzoate, mass spectrum (m/e); 403 10) M+.

Workup

temperatureAfter cooling to room temperature the mixture
filtrationis filtered
dissolutionthe filtrate is dissolved in 200 ml of ethyl acetate
washThe solution is washed four times with 50 ml of water each time
customthe combined organic phases are dried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f562dbd76be64c8e844be7b90a49534f
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05183492

Reaction notes

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