Dichloromethane → (R)-8-Acetyl-2-(1-amino-ethyl)-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 2223146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223146
C(OC(=O)[NH:7][C@@H:8]([C:10]1[N:11]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=2)[C:12](=[O:23])[C:13]2[CH2:19][CH2:18][CH2:17][N:16]([C:20](=[O:22])[CH3:21])[C:14]=2[N:15]=1)[CH3:9])(C)(C)C.ClCCl>FC(F)(F)C(O)=O>[C:20]([N:16]1[C:14]2[N:15]=[C:10]([C@H:8]([NH2:7])[CH3:9])[N:11]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=3)[C:12](=[O:23])[C:13]=2[CH2:19][CH2:18][CH2:17]1)(=[O:22])[CH3:21]

Komponenten

4

Edukt 2

HCID 6344DichloromethaneHCID 58617397(R)-{1-[8-Acetyl-3-(4-ethoxy-phenyl)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 58617407(R)-8-Acetyl-2-(1-amino-ethyl)-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

D3 (268 mg, 0.59 mmol) was dissolved in 1:1 trifluoroacetic acid:dichloromethane (10 mL). The reaction stirred at room temperature for 30 min. The solvent was removed in vacuo, then 10% aqueous ammonium hydroxide was added until the aqueous pH=9. The aqueous layer was extracted three times with dichloromethane, then the combined organic layer was washed with saturated aqueous sodium bicarbonate and brine. It was dried over magnesium sulfate, filtered, and concentrated in vacuo, recovering 170 mg of D4. MS (MH+): 357.1. 1H NMR (400 MHz; CDCl3; T=298 K): δ 7.13 (ddd, 2H, J=18.9, 1.4, 1.1 Hz), 7.02 (ddd, 2H, J=9.0, 1.2, 0.8 Hz), 4.09 (dq, 2H, J=6.9, 1.2 Hz), 3.98-3.80 (ddq, 2H, J=62.6, 5.3, 1.0 Hz), 3.73 (dd, 1H, J=6.6, 1.2 Hz), 2.60 (s, 3H), 1.92 (m, 2H), 1.82 (broad s, 2H), 1.45 (ddd, 3H, J=8.3, 6.1, 1.3 Hz), 1.28-1.21 (m, 5H) ppm.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. addition10% aqueous ammonium hydroxide was added until the aqueous pH=9
  3. extractionThe aqueous layer was extracted three times with dichloromethane
  4. washthe combined organic layer was washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialIt was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customrecovering 170 mg of D4

Quellen und Nachweise

ORD-Eintrag
ord-63b4fc9a6f684159bc2557e5bb0040df
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375102B2

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