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Hydrochloric Acid → 6-Amino-5-[(6-hydroxy-2,5,7,8-tetramethyl-2-chromanylmethyl)amino]-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedione

HRID 399424
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 399424
C([O:4][C:5]1[C:6]([CH3:37])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH3:36])([C:17]([NH:19][C:20]1[C:21](=[O:35])[N:22]([CH3:34])[C:23](=[O:33])[N:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:25]=1[NH2:26])=O)[CH2:9][CH2:8]2)(=O)C.Cl>C1COCC1>[NH2:26][C:25]1[N:24]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:23](=[O:33])[N:22]([CH3:34])[C:21](=[O:35])[C:20]=1[NH:19][CH2:17][C:10]1([CH3:36])[CH2:9][CH2:8][C:7]2[C:12](=[C:13]([CH3:16])[C:14]([CH3:15])=[C:5]([OH:4])[C:6]=2[CH3:37])[O:11]1
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 572790375-(6-Acetoxy-2.5,7,8-tetramethvlchroman-2-carboxamido)-6-amino-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedione

Produkt 1

HCID 1317208806-Amino-5-[(6-hydroxy-2,5,7,8-tetramethyl-2-chromanylmethyl)amino]-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedioneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The compound of Example 14 (64 mg, 1.0 mmol) was dissolved in THF (10 mL). To the resultant solution was added borane-methyl sulfide complex (10 M, 0.24 mL, 2.4 mmol). The resultant reaction mixture was refluxed for 5 h. To the resultant was added 1N hydrochloric acid (2.4 mL) under ice-cooling. The resultant mixture was refluxed for 2 h, followed by concentration under reduced pressure. The residue was extracted with dichloromethane after addition of 1N aqueous solution of sodium hydroxide. The organic layer was washed with 10% aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized by addition of ethyl acetate and ether to give the title compound (yield 35%).

Aufarbeitung

  1. customThe resultant reaction mixture
  2. temperaturewas refluxed for 5 h
  3. temperaturecooling
  4. concentrationfollowed by concentration under reduced pressure
  5. extractionThe residue was extracted with dichloromethane
  6. additionafter addition of 1N aqueous solution of sodium hydroxide
  7. washThe organic layer was washed with 10% aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was crystallized by addition of ethyl acetate and ether

Quellen und Nachweise

ORD-Eintrag
ord-706e3c1f043d4f1c82e5b7ec86c93210
Quelldatensatz
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05821247

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