Methanol → 2-(3-Methoxyphenyl)-5-octyloxypyrimidine
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:23]O>>[CH3:23][O:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1Participants
Procedure
5.52 g (21.05 mmol) of triphenylphosphine and 3.67 g (21.05 mmol) of diethyl azodicarboxylate are stirred at 0° C. for 30 minutes in 100 ml of tetrahydrofuran. 3.90 g (14.03 mmol) of 2-(3-benzyloxyphenyl)-5-hydroxypyrimidine and 2.74 g (21.05 mmol) of 1-octanol are subsequently added, and the resultant solution is stirred at room temperature for 18 hours. Evaporation to dryness and purification by chromatography (silica gel/dichloromethane) give 4.25 g of 2-(3-benzyloxyphenyl)-5-octyloxypyrimidine. ##STR29## Removal of the benzyl protecting group by hydrogenation analogously to Example 1 gives 2-(3-hydroxyphenyl)-5-octyloxypyrimidine. ##STR30## 2-(3-Hydroxyphenyl)-5-octyloxypyrimidine is reacted with methanol analogously to Example 1 to give 2-(3-methoxyphenyl)-5-octyloxypyrimidine. ##STR31## The compound has the phase sequence: X43 I
Sources & evidence
- ORD record
- ord-b4e72a92c6b944298b6b819c83d705ff
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05447656
Reaction notes
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