Sodium hydride → {2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl}-1-piperidinecarboxylate

HRID 1722962Notes

Reaction equation

HRID 1722962 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([F:22])[CH:3]=1.Cl[C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25].[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([F:22])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:6][C:7]=1[O:8][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2420851-Piperidinecarbonyl chlorideHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 86743320{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl}-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

using 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione with N-chlorocarbonyl-piperidine and sodium hydride in dimethylformamide there is obtained {2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H) -pyrimidinyl]-4-fluorophenyl}-1-piperidinecarboxylate, 1 -NMR (CDCl3, 400 MHz): 7.33 ppm (d,1H), 7.25 ppm (d,1H), 6.34 ppm (s,1H), 3.57°-3.69 ppm (m,2H), 3.53 ppm (d,3H), 3.44°-3.56 ppm (m,2H), 1.56°-1.70 ppm (m,6H);

Sources & evidence

ORD record
ord-5c2908833f344816a9934b6749aa8fcc
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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