Acetic Acid → (5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol
Reaction equation
C([O-])(=O)CO.[NH2:6][C:7]1[NH:11][N:10]=[C:9]([CH2:12][OH:13])[N:8]=1.[CH3:14][C:15](=O)[CH2:16][C:17](=O)[CH3:18].C(O)(=O)C>C(Cl)Cl.CCO>[CH3:14][C:15]1[CH:16]=[C:17]([CH3:18])[N:11]2[N:10]=[C:9]([CH2:12][OH:13])[N:8]=[C:7]2[N:6]=1Participants
7
Procedure
To a 2 L, 3-neck flask was charged glycolate salt of (5-amino-1H-1,2,4-triazol-3-yl)methanol (99.93 g, 0.526 mol), 2,4 pentanedione (0.578 mols, 60 mL), acetic acid (6.70 mL), and EtOH (550 mL). The mixture was heated to a slight reflux. One hour after adding the reagents, the resulting solution was cooled to ambient temperature, and CH2Cl2 (500 mL) and Celite (25.03 g) were added. After stirring for 1 h, the mixture was filtered through a 4″ Buchner funnel packed with celite (20 g) and rinsed with EtOH (100 mL). The solution was distilled to 5 vols then cooled to 0° C. for 1-2 hours. The slurry was filtered and the cake was rinsed with cold EtOH (2×100 mL). The solids were dried to provide 76.67 g (81.7%) of the title compound.
Workup
- temperatureThe mixture was heated to a slight reflux
- additionOne hour after adding the reagents
- filtrationthe mixture was filtered through a 4″ Buchner funnel
- washrinsed with EtOH (100 mL)
- distillationThe solution was distilled to 5 vols
- temperaturethen cooled to 0° C. for 1-2 hours
- filtrationThe slurry was filtered
- washthe cake was rinsed with cold EtOH (2×100 mL)
- customThe solids were dried
Sources & evidence
- ORD record
- ord-72d5d85e8287494d8dba65051da7896a
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807838B2
Reaction notes
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