Ethanol → HCID 86628368, compound

HRID 657108Notes

Reaction equation

HRID 657108 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]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 57927969HCID 57927969, compound

Product 1

HCID 86628368HCID 86628368, compound

Procedure

3-{4-Amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanamide (0.175 g, 0.58 mmol) was dissolved in EtOH 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, neutralised to pH9 with K2CO3 solution 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) with DCM/(DCM:MeOH:NH4OH) 90:10:1 to yield an additional 0.11 g of the desired compound.

Workup

  1. customHCl gas was bubbled through the solution until saturated
  2. temperatureThe solution was heated
  3. temperatureat reflux for 2 h
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residue was dissolved in water, neutralised to pH9 with K2CO3 solution
  6. extractionextracted with EtOAc (3×)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8910aa5e5a6f478f82ae07436e297857
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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