4-Fluorophenol → HCID 59753903, compound

HRID 750873Notes

Reaction equation

HRID 750873 reaction equation
CS(C1N=C(OC)C(C2C=CC(Cl)=CC=2)=C(C2C=CC(Cl)=CC=2Cl)N=1)(=O)=O.[CH3:28][O:29][C:30]1[N:35]=[C:34](S(C)(=O)=O)[C:33]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)=[C:32]([C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][C:48]=2[Cl:54])[N:31]=1.C([Li])CCC.[F:60][C:61]1[CH:66]=[CH:65][C:64]([OH:67])=[CH:63][CH:62]=1>>[CH3:28][O:29][C:30]1[N:35]=[C:34]([O:67][C:64]2[CH:65]=[CH:66][C:61]([F:60])=[CH:62][CH:63]=2)[C:33]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)=[C:32]([C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][C:48]=2[Cl:54])[N:31]=1

Participants

5

Reactant 4

HCID 97324-FluorophenolHCID 10366150HCID 10366150, compoundHCID 10456101HCID 10456101, compoundHCID 178418339Butyllithium

Product 1

HCID 59753903HCID 59753903, compound

Procedure

A mixture of 2-(methylsulfonyl)-4-methoxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-pyrimidine and 2-methoxy-4-(methylsulfonyl)-5-(4-chloro-phenyl)-6-(2,4-dichlorophenyl)-pyrimidine (Example 113) was reacted with 1.1 equivalents each of n-butyl lithium and 4-fluorophenol by the procedure described in Reference Example 6 and 7 to afford a mixture of 2-(4-fluorophenyloxy)-4-methoxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl) and 2-methoxy-4-(4-fluorophenyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine which was separated by flash column chromatography on silica gel. Only the LRf was characterized. 2-methoxy-4-(4-fluorophenyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (LRf): HPLC/MS: m/e=475 (M++1); Rt=4.61 min. 1H-NMR 400 MHz (CDCl3): 3.89 (s, 3H), 6.75-6.79 (m, 2H), 6.91-6.96 (m, 2H), 7.10-7.34 (m, 7H).

Workup

  1. customto afford
  2. customwas separated by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-18e3ef32751842a787a16edfba0f365f
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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