Dimethyl Sulfate → 3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-1,5-dimethyl-2,4(1H,3H)-pyrimidinedione
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][N:18]2[C:23](=[O:24])[C:22]([CH3:25])=[CH:21][NH:20][C:19]2=[O:26])[CH2:11][CH2:10]1.S(OC)(O[CH3:31])(=O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][N:18]2[C:23](=[O:24])[C:22]([CH3:25])=[CH:21][N:20]([CH3:31])[C:19]2=[O:26])[CH2:13][CH2:14]1Participants
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-methyl-2,4(1H,3H)-pyrimidinedione (550 mg, 1.53 mmol), prepared as in Example 32, dimethyl sulfate (193 mg, 1.53 mmol) and 0.1N tetrabutylammonium fluoride (100 mL, 10 mmol in THF) was stirred 4 hours at 25° C. The reaction mixture then was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with ethyl acetate to give 3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-1,5-dimethyl-2,4(1H,3H)-pyrimidinedione, as an oil. The free base was recrystallized from a solution of hydrochloric acid in alcohol to give 3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-1,5-dimethyl-2,4(1H,3H)-pyrimidinedione hydrochloride, m.p. 256°-258° C. Anal.: Calcd. for C20H28N4O3.(HCl)2 : C, 53.93; H, 6.79; N, 12.58%; Found: C, 54.05; H, 6.87; N, 12.58%.
Workup
- concentrationThe reaction mixture then was concentrated in vacuo
- customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate
Sources & evidence
- ORD record
- ord-c6777ca6bf9e4d489fff91ab43f63d29
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05859014
Reaction notes
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