Identification | Back Directory | [Name]
5-allylpyriMidine-4,6-diol | [CAS]
16019-30-0 | [Synonyms]
5-allylpyriMidine-4,6-diol 5-Allyl-4-hydroxy-1H-pyrimidin-6-one 5-ALLYL-6-HYDROXYPYRIMIDIN-4(3H)-ONE 5-allyl-6-hydroxy-1H-pyrimidin-4-one 4-Hydroxy-5-prop-2-enyl-1H-pyrimidin-6-one 4(3H)-Pyrimidinone, 6-hydroxy-5-(2-propen-1-yl)- | [Molecular Formula]
C7H8N2O2 | [MDL Number]
MFCD13192751 | [MOL File]
16019-30-0.mol | [Molecular Weight]
152.15 |
Hazard Information | Back Directory | [Synthesis]
Step 2: Ethanol (100 mL) was added to a 500 mL round-bottomed flask under nitrogen protection, followed by the slow addition of sodium metal (4.5 g). After stirring at room temperature until the sodium metal was completely dissolved, the reaction mixture was cooled to 0 °C. Diethyl 2-allylmalonate (12 g) and formamidine acetate (6.24 g) were added sequentially, maintaining a nitrogen atmosphere. The reaction was continued to be stirred at room temperature for 24 hours. Upon completion of the reaction, the reaction was quenched sequentially with acetic acid (20 mL) and water (100 mL). The white precipitate was collected by filtration, washed sequentially with water (4 × 50 mL) and methanol (2 × 50 mL), and dried under vacuum to afford 5-allylpyrimidine-4,6-diol (4 g) as a white solid. NMR hydrogen spectrum (DMSO-d6): δ 2.96 (d, 2H), 4.85 (dd, 1H), 4.91 (dd, 1H), 5.76 (dd, 1H), 7.89 (s, 1H), 11.64 (bs, 2H). | [References]
[1] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3639 - 3648 [2] Patent: US2010/144758, 2010, A1. Location in patent: Page/Page column 65-66 [3] Patent: WO2013/138436, 2013, A1. Location in patent: Page/Page column 61 |
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