1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone → 3-(4,5-dichloropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
Reaction equation
[Li+].CC([N-]C(C)C)C.[Cl:9][C:10]1[C:15]([Cl:16])=[C:14]([CH2:17][CH3:18])[N:13]=[CH:12][N:11]=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[C:27](=[O:34])[CH2:28][N:29]1[CH:33]=[N:32][CH:31]=[N:30]1>C1COCC1>[Cl:9][C:10]1[C:15]([Cl:16])=[C:14]([CH:17]([CH3:18])[C:27]([C:21]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=2[F:19])([OH:34])[CH2:28][N:29]2[CH:33]=[N:32][CH:31]=[N:30]2)[N:13]=[CH:12][N:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of LDA (13.6 mmol) in THF (50 ml) (prepared by a similar method to that used in Example 1) at -70° C. was added dropwise 4,5-dichloro-6-ethylpyrimidine (the product of part (ii)) (2.37 g, 13.3 mmol) and the resulting solution was stirred at this at this temperature for 10 minutes. A solution of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (2.97 g 13.3 mmol) in THF (50 ml) was added to the reaction mixture at such a rate so as to maintain the reaction temperature below -50° C. After stirring at -70° C. for 1 hour and at -50° C. for a further 1 hour the reaction was quenched by the addition of 10% aqueous acetic acid (11 ml).
Workup
- customat -70° C.
- temperatureto maintain the reaction temperature below -50° C
- stirringAfter stirring at -70° C. for 1 hour and at -50° C. for a further 1 hour the reaction
- customwas quenched by the addition of 10% aqueous acetic acid (11 ml)
Sources & evidence
- ORD record
- ord-fda5cccc3fd04ce19df4ac335e84199c
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05567817
Reaction notes
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