5-benzyl-6-methyl-2-methylsulfanyl-1H-pyrimidin-4-one → 5-benzyl-6-methyl-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-4-one
Reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[NH:10][CH:9]=[N:8][C:7]=1[CH3:11].[CH2:12]([C:19]1[C:20](=[O:28])[NH:21][C:22](SC)=[N:23][C:24]=1[CH3:25])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:11][C:7]1[N:8]=[CH:9][NH:10][C:6]=1[CH2:5][S:4][CH2:3][CH2:2][NH:1][C:22]1[NH:21][C:20](=[O:28])[C:19]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:24]([CH3:25])[N:23]=1Participants
Procedure
5-Benzyl-6-methylthiouracil (6.0 gms) and sodium hydroxide (1.06 gms) were dissolved in water (30 mls). The solution was cooled and ethanol (60 mls) and methyl iodide (3.67 gms) added with stirring. The mixture was heated at 60° C. for 1/2 hour, cooled and the resulting solid collected and water-washed. A second crop of solid was obtained by acidification of the filtrate to pH=4 with acetic acid. Recrystallisation from ethanol produced 5-benzyl-6-methyl-2-methylthio-4-pyrimidone (5.53 gms) m.p.=220°-221.5° C. An intimate mixture of 5-(2-aminoethyl)thiomethyl-4-methylimidazole (1.28 gms) and 5-benzyl-6-methyl-2-methylthio-4-pyrimidone (1.84 gms) was heated at 150°-160° C. (oil-bath temperature) for 41/2 hours. The mixture was cooled, washed with water and recrystallised from isopropanol to give 2-[-2-(4-methyl-5-imidazolylmethylthio)ethylamino]-5-benzyl-6-methyl-4-pyrimidone (1.82 gms) m.p.=140°-141.5° C.
Workup
- temperaturewas heated at 150°-160° C. (oil-bath temperature) for 41/2 hours
- temperatureThe mixture was cooled
- washwashed with water
- customrecrystallised from isopropanol
Sources & evidence
- ORD record
- ord-8934c766dfd14fe49b3de591ee0043f3
- Source dataset
- uspto-grants-1983_02
- Patent number
- US04374251
Reaction notes
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