[CH3:1][C:2]([CH3:14])([CH3:13])[C:3](=[O:12])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[C:16]1[CH:17]=[N:18][CH:19]=[N:20][CH:21]=1.C([Li])CCC.[Cl-].[NH4+]>O1CCCC1.CCOCC.CCCCCC>[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([C:16]1[CH:17]=[N:18][CH:19]=[N:20][CH:21]=1)([OH:12])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
A solution of 19.2 g (0.1 mol) of 3,3-dimethyl-1-phenoxy-butan-2-one in 110 ml of absolute tetrahydrofuran and 70 ml of absolute ether was cooled to -120° C. under a dry nitrogen atmosphere. A solution of 15.7 g (0.1 mol) of 5-bromopyrimidine in 50 ml of absolute tetrahydrofuran was added dropwise. 60 ml of a 15% strength solution of n-butyl-lithium (containing about 0.14 mol) in n-hexane were then slowly added dropwise at -120° C. The mixture was stirred further, first for 2 hours at a temperature of about -110° C. and then overnight at -78° C. The reaction mixture was then warmed to room temperature, mixed with 100 ml of 10% strength ammonium chloride solution and concentrated in vacuo. The aqueous suspension was then extracted with ethyl acetate. The ethyl acetate extract was washed successively twice with 1N hydrochloric acid, twice with water and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated. The residue was recrystallized from cyclohexane. 10.5 g (39% of theory) of 3,3-dimethyl-1-phenoxy-2-pyrimidin-5-yl-butan-2-ol of melting point 127°-129° C. were obtained.
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