(-)-(4-(1-Acetoxy-ethyl)phenyl)-5-decyloxypyrimidine → 2-(4-(1-Hydroxyethyl)phenyl)-5-decyloxypyrimidine

HRID 1161

Reaction equation

C([O:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:15][N:14]=2)=[CH:9][CH:8]=1)[CH3:6])(=O)C>CO.[OH-].[Na+]>[OH:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:15][N:14]=2)=[CH:11][CH:12]=1)[CH3:6]

Participants

Conditions

Temperature: 30 °C

Procedure

4 g of the above product (-)-(4-(1-acetoxyethyl) phenyl)-5-decyloxypyrimidine was dissolved in a mixture of 50 ml of methanol and 10 ml of a 20% sodium hydroxide solution, stirred at 30° C. for 2 hours and hydrolyzed, and the resulting reaction solution was extracted by adding 200 ml of water and 200 ml of toluene, followed by liquid separation. The obtained organic layer was dried over anhydrous magnesium sulfate and cleared of solvent in vacuo to yield 3.5 g of (-)-(4-(1-hydroxyethyl) phenyl)-5-decyloxypyrimidine as a white solid.

Workup

customhydrolyzed, and the resulting reaction solution
extractionwas extracted
additionby adding 200 ml of water and 200 ml of toluene
customfollowed by liquid separation
dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record: ord-01a269bda00c4ee495d089d890ae2b6c
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723610

Linked notes

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