Ethanol → HCID 86628368, compound
Reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][C:10](N)=[O:11])=[C:6]([Cl:13])[N:5]=[C:4](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[CH3:22][CH2:23][OH:24]>>[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:24][CH2:23][CH3:22])=[O:11])=[C:6]([Cl:13])[N:5]=[C:4](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1Participants
Procedure
3-{4-Amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanamide (0.175 g, 0.58 mmol) was dissolved in EtOH (15 mL) and HCl gas was bubbled through the solution until saturated. The solution was heated at reflux for 2 h, cooled to ambient temperature and concentrated under vacuum. The residue was dissolved in water and extracted with EtOAc (3×). The organic layers were combined, dried over Na2SO4, filtered and concentrated under vacuum to yield ethyl 3-{4-amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanoate as a white solid. LCMS: m/z 332.2 (MH+). This product was then dissolved in DMF (5 mL), treated with K2CO3 (0.16 g, 1.16 mmol) and heated at 75° C. for 30 minutes. The solution was cooled, diluted with water and extracted with Et2O (3×). The organic layer was dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was then purified by column chromatography (silica gel) to yield an additional 0.11 g of the desired compound as an off-white solid.
Workup
- customHCl gas was bubbled through the solution until saturated
- temperatureThe solution was heated
- temperatureat reflux for 2 h
- concentrationconcentrated under vacuum
- dissolutionThe residue was dissolved in water
- extractionextracted with EtOAc (3×)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-bdd44c884bfd46b4bec085097b823315
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709483B2
Reaction notes
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