Triphenylphosphine → 3-Benzoyl-1-(5-trityloxypentyl)-1H-pyrimidine-2,4-dione

HRID 908514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908514
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]O)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:46]([N:54]1[C:59](=[O:60])[CH:58]=[CH:57][NH:56][C:55]1=[O:61])(=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCCCCC.CCOC(C)=O>[C:46]([N:54]1[C:59](=[O:60])[CH:58]=[CH:57][N:56]([CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][O:39][C:20]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:55]1=[O:61])(=[O:53])[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5695133-BenzoyluracilHCID 5363146Diisopropyl azodicarboxylateHCID 119616005-Trityloxypentanol

Produkt 1

HCID 114975923-Benzoyl-1-(5-trityloxypentyl)-1H-pyrimidine-2,4-dioneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

Polymer supported triphenyl phosphine (2.5 eq, 3 mmol/g loading) was swelled in dry THF for 15 minutes then the alcohol 14 (1 eq, 300 mg) and the N3-benzoyluracil (1.5 eq) were added into the suspension, which was shaken at room temperature under atmosphere of nitrogen. A solution of DIAD (2 eq) in THF was added slowly into the suspension. The reaction was shaken overnight until the disappearance of the alcohol was observed by TLC. The resin was then filtered off and washed with THF (5 ml). The solvent was removed under reduced pressure to afford a residue which was taken in a mixture of Hexane/EtOAc (50:50). The formed white precipitate was removed and the solution was concentrated to an orange oil and purified by flash chromatography using a mixture of Hexane/EtOAc (40:60) as eluent which gave the title compound (250 mg, 53%).

Aufarbeitung

  1. filtrationThe resin was then filtered off
  2. washwashed with THF (5 ml)
  3. customThe solvent was removed under reduced pressure
  4. customto afford a residue which
  5. customThe formed white precipitate was removed
  6. concentrationthe solution was concentrated to an orange oil
  7. custompurified by flash chromatography
  8. additiona mixture of Hexane/EtOAc (40:60) as eluent which

Quellen und Nachweise

ORD-Eintrag
ord-fa6fd072290c4cc4826ee0cf2277a172
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017620B2

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