Water → 4-Chloro-6-(3-methylbut-1-oxy)-2-phenylpyrimidine

HRID 1742755

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[OH2:15]>CC(C)CCO>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([O:15][CH2:11][CH2:10][CH:9]([CH3:14])[CH3:4])[CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

The reaction is carried out under an argon protective-gas atmosphere. A solution of 6.7 g (60.5 mmol) of sodium t-amylate in 50 ml of 3-methylbutanol is added dropwise to a solution, cooled to 0° C., of 12.4 g of 4,6-dichloro-2-phenylpyrimidine in 50 ml of 3-methylbutanol. The reaction mixture is allowed to warm to 25° C. overnight. Thin-layer chromatography shows the absence of starting material. The reaction mixture is poured into 180 ml of water and extracted three times with 80 ml of ethyl acetate. Combined organic phases are washed with water, dried using MgSO4 and filtered. Removal of the solvent gives 14.6 g (96% of theory) of the title compound.

Workup

extractionextracted three times with 80 ml of ethyl acetate
washCombined organic phases are washed with water
customdried
filtrationfiltered
customRemoval of the solvent

Sources & evidence

ORD record: ord-4992921d69164201ae402c37e8c994ce
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05340701

Linked notes

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