Triphenylphosphine → 3-Butyl-8-chloro-1-{3-[5-(phenylmethyl)-1,2,4-oxadiazol-3-yl]propyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097680
[C:1]1([CH2:7][C:8]2[O:12][N:11]=[C:10]([CH2:13][CH2:14][CH2:15]O)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([N:21]1[C:29]2[N:28]=[C:27]([Cl:30])[N:26](CC=C)[C:25]=2[C:24](=[O:34])[NH:23][C:22]1=[O:35])[CH2:18][CH2:19][CH3:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C1COCC1>[CH2:17]([N:21]1[C:29]2[N:28]=[C:27]([Cl:30])[NH:26][C:25]=2[C:24](=[O:34])[N:23]([CH2:15][CH2:14][CH2:13][C:10]2[N:9]=[C:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:12][N:11]=2)[C:22]1=[O:35])[CH2:18][CH2:19][CH3:20]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 592995823-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dioneHCID 593958023-[5-(Phenylmethyl)-1,2,4-oxadiazol-3-yl]-1-propanol

Produkt 1

HCID 593958083-Butyl-8-chloro-1-{3-[5-(phenylmethyl)-1,2,4-oxadiazol-3-yl]propyl}-3,7-dihydro-1H-purine-2,6-dioneAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-[5-(phenylmethyl)-1,2,4-oxadiazol-3-yl]-1-propanol (594 mg, 2.7 mmol) in THF (25 ml) was treated with 3-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (700 mg, 2.48 mmol) and PPh3 (779 mg, 2.97 mmol) under nitrogen. DBAD (684 mg, 2.97 mmol) was added in one portion and the reaction left to react for 60 h. The mixture was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated. MeOH was added to the residue and then passed down an aminopropyl column with the product eluting with 2-4% AcOH/MeOH. Product fractions were combined and concentrated. The off-white residue was recrystallised from EtOAc:cyclohexane (1:1), giving the title compound as a white solid (696 mg, 63%).

Aufarbeitung

  1. waitthe reaction left
  2. customto react for 60 h
  3. customThe mixture was partitioned between 2M HCl (aq) and EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. additionMeOH was added to the residue
  9. washeluting with 2-4% AcOH/MeOH
  10. concentrationconcentrated
  11. customThe off-white residue was recrystallised from EtOAc:cyclohexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ab733ef603b9428aadc0512de51d7dc8
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

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