2-Chloro-3-(trifluoromethyl)pyridine → 2-[4-Chloro-2-fluoro-5-(3-trifluoromethyl-2-pyridyloxy)phenyl]-6,7-dihydropyrrolo[1,2-c]pyrimidine-1,3(2H,5H)-dione

HRID 1017172Notes

Reaction equation

HRID 1017172 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]3[CH2:16][CH2:17][CH2:18][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.Cl[C:22]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=1.ClC1C(OC2N=CC=CN=2)=CC(N2C(=O)N3CCCCN3C2=S)=C(F)C=1>>[Cl:1][C:2]1[C:7]([O:8][C:22]2[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]3[CH2:16][CH2:17][CH2:18][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1

Participants

4

Reactant 3

HCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 184029112-(4-Chloro-2-fluoro-5-hydroxyphenyl)-6,7-dihydropyrrolo[1,2-c]pyrimidine-1,3(2H,5H)-dioneHCID 184029602-[4-chloro-2-fluoro-5-(2-pyrimidyloxy)phenyl]hexahydro-3-thioxo-1H-[1,2,4]triazolo[1,2-a]pyridazin-1-one

Product 1

HCID 184029542-[4-Chloro-2-fluoro-5-(3-trifluoromethyl-2-pyridyloxy)phenyl]-6,7-dihydropyrrolo[1,2-c]pyrimidine-1,3(2H,5H)-dioneYield 90%

Procedure

This was synthesized from 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-6,7-dihydro-pyrrolo-[1,2-c]pyrimidine-1,3(2H,5H)-dione and 2-chloro-3-trifluoromethylpyridine in 90% yield under similar conditions described below for the preparation of 2-[4-chloro-2-fluoro-5-(2-pyrimidyloxy)phenyl]hexahydro-3-thioxo-1H-[1,2,4]triazolo[1,2-a]pyridazin-1-one (Example 10.3) (compound (8-29).

Sources & evidence

ORD record
ord-287a49306ba2436c8b31b3f7d9415549
Source dataset
uspto-grants-2002_11
Patent number
US06479435B1

Reaction notes

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