Water → HCID 86754753, compound
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:13][CH:14]=2)[N:5]=[CH:4][N:3]=1.[F:19][C:20]([F:32])([F:31])[C:21]1[C:26]([N+]([O-])=O)=[CH:25]C=[C:23]([OH:30])[CH:22]=1.C(=O)([O-])[O-:34].[K+].[K+].[OH2:39].C[N:41]([CH3:44])C=O>>[F:19][C:20]([F:31])([F:32])[C:21]1[CH:26]=[CH:25][C:44]([N+:41]([O-:34])=[O:39])=[C:23]([O:30][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:13][CH:14]=3)[N:5]=[CH:4][N:3]=2)[CH:22]=1.[F:19][C:6]1[CH:7]=[C:2]([F:1])[N:3]=[CH:4][N:5]=1Participants
6
Procedure
A mixture of 4-fluoro-6-[(α,α,α-trifluoro-m-tolyl)oxy]pyrimidine (87.4 g, 0.34 mol), α,α,α-trifluoro-4-nitro-m-cresol (84.9 g, 0.41 mol) and potassium carbonate (55 g, 0.40 mol) in N,N-dimethylformamide (1 L) is stirred at room temperature until the reaction is complete by thin layer chromatography analysis (8:1 hexanes/ethyl acetate). The reaction mixture is then poured into water and the resultant aqueous mixture is extracted with diethyl ether. The organic extract is dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a solid. The solid is recrystallized from an ethyl acetate/heptane solution to give the title product as a white solid (108 g, 71% yield).
Workup
- extractionthe resultant aqueous mixture is extracted with diethyl ether
- extractionThe organic extract
- dry with materialis dried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- customto obtain a solid
- customThe solid is recrystallized from an ethyl acetate/heptane solution
Sources & evidence
- ORD record
- ord-190578119ec44e90b4128ad5272bbc6e
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06087498
Reaction notes
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