Ethanol → 5-benzyl-6-methyl-2-methylsulfanyl-1H-pyrimidin-4-one

HRID 1758551Notes

Reaction equation

[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11](=[S:15])[NH:12][C:13]=1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:19](O)C.CI>O>[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11]([S:15][CH3:19])=[N:12][C:13]=1[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

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

temperatureThe solution was cooled
temperaturecooled
customthe resulting solid collected
washwater-washed
customA second crop of solid was obtained by acidification of the filtrate to pH=4 with acetic acid
customRecrystallisation from ethanol

Sources & evidence

ORD record: ord-3f0744daee5346288ca7ff291f9656bb
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374251

Reaction notes

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