Phosphorus oxychloride → 2-chloro-1-(4-chloro-2-fluoro-5-isopropoxyphenyl)-5-fluoro-4-trifluoromethyl-6(1H)-pyrimidinone

HRID 1193940Notes

Reaction equation

HRID 1193940 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:17](=[O:18])[C:16]([F:19])=[C:15]([C:20]([F:23])([F:22])[F:21])[NH:14][C:13]2=O)=[C:4]([F:25])[CH:3]=1.P(Cl)(Cl)([Cl:28])=O>N1C=CC=CC=1>[Cl:28][C:13]1[N:12]([C:5]2[CH:6]=[C:7]([O:8][CH:9]([CH3:11])[CH3:10])[C:2]([Cl:1])=[CH:3][C:4]=2[F:25])[C:17](=[O:18])[C:16]([F:19])=[C:15]([C:20]([F:23])([F:22])[F:21])[N:14]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20026119HCID 20026119, compound

Product 1

HCID 212707052-chloro-1-(4-chloro-2-fluoro-5-isopropoxyphenyl)-5-fluoro-4-trifluoromethyl-6(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

using 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-5-fluoro-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione with phosphorus oxychloride and pyridine within 15 minutes at 20°-40° C. and thereafter for 1 hour at 70° C. there is obtained 2-chloro-1-(4-chloro-2-fluoro -5-isopropoxyphenyl)-5-fluoro-4-trifluoromethyl-6(1H)-pyrimidinone, 1H-NMR (CDCl3, 60 MHz): 7.42 ppm (d,1H), 6.84 ppm (d,1H), 4.50 ppm (m,1H), 1.44 ppm (d,6H);

Workup

  1. customwithin 15 minutes
  2. customat 20°-40° C.

Sources & evidence

ORD record
ord-bcc0e03d071a43f18734c7c7a3118cc2
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

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