Trifluoroacetic acid → (R)-{1-[3-(4-Ethoxy-phenyl)-8-methyl-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

HRID 2223154Notes

Reaction equation

HRID 2223154 reaction equation
[NH2:1][C@@H:2]([C:4]1[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=2)[C:6](=[O:15])[C:7]2[CH2:13][CH2:12][CH2:11][N:10]([CH3:14])[C:8]=2[N:9]=1)[CH3:3].FC(F)(F)[C:27]([OH:29])=[O:28]>ClCCl>[C:7]([O:29][C:27](=[O:28])[NH:1][C@@H:2]([C:4]1[N:5]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH3:24])=[CH:20][CH:21]=2)[C:6](=[O:15])[C:7]2[CH2:13][CH2:12][CH2:11][N:10]([CH3:14])[C:8]=2[N:9]=1)[CH3:3])([CH3:13])([CH3:8])[CH3:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58617394HCID 58617394, compound

Product 1

HCID 58617377(R)-{1-[3-(4-Ethoxy-phenyl)-8-methyl-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-2-(1-Amino-ethyl)-3-(4-ethoxy-phenyl)-8-methyl-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one (G2) To a solution of 110 mg G1 (0.26 mmol, 1.00 equiv.) dissolved in 2 mL dichloromethane cooled by an ice-bath was added 4 mL trifluoroacetic acid all at once. The reaction was equilibrated to room temperature. After 40 min. the reaction was concentrated in vacuo and the concentrate was partitioned between 25 mL each dichloromethane and saturated aqueous sodium bicarbonate. The aqueous separation was extracted again with 25 mL dichloromethane. Combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo to afford G4 as a faint yellow glassy solid, 83 mg. The product was used in the next step without further purification.

Workup

  1. temperaturecooled by an ice-bath
  2. customwas equilibrated to room temperature
  3. concentrationAfter 40 min. the reaction was concentrated in vacuo
  4. customthe concentrate was partitioned between 25 mL each dichloromethane and saturated aqueous sodium bicarbonate
  5. customThe aqueous separation
  6. extractionwas extracted again with 25 mL dichloromethane
  7. dry with materialCombined organic extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford G4 as a faint yellow glassy solid, 83 mg
  11. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-2e753fc85fd04163af7f0c7617e99b22
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

Loading…