Tin tetrachloride → Benzoic acid 2-(5-amino-7-oxo-6,7-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-[2-(diethoxy-phosphoryl)-vinyl]-tetrahydro-furan-3-yl ester

HRID 2191015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191015
[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][N:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].C(NC1N=C2C(N=CN2[CH:25]2[CH:29]([O:30][C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:28][CH:27]([CH:39]=[CH:40][P:41]([O:46][CH2:47][CH3:48])([O:43][CH2:44][CH3:45])=[O:42])[O:26]2)=C(OC(=O)N(C2C=CC=CC=2)C2C=CC=CC=2)N=1)(=O)C.C(OP(C=CC1CC(C(=O)C2C=CC=CC=2)C(C(=O)C2C=CC=CC=2)O1)(=O)OCC)C.Cl[Sn](Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>CC#N>[NH2:3][C:2]1[NH:1][C:10](=[O:11])[C:9]2[N:8]=[N:7][N:6]([CH:25]3[CH:29]([O:30][C:31](=[O:38])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:28][CH:27]([CH:39]=[CH:40][P:41]([O:43][CH2:44][CH3:45])([O:46][CH2:47][CH3:48])=[O:42])[O:26]3)[C:5]=2[N:4]=1

Komponenten

7

Edukt 5

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 72247319Benzoic acid 2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-[2-(diethoxy-phosphoryl)-vinyl]-tetrahydro-furan-3-yl esterHCID 86641113[2-(4,5-Dibenzoyl-tetrahydro-furan-2-yl)-vinyl]-phosphonic acid diethyl esterHCID 178508264HCID 178508264, Verbindung

Produkt 1

HCID 136381447Benzoic acid 2-(5-amino-7-oxo-6,7-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-[2-(diethoxy-phosphoryl)-vinyl]-tetrahydro-furan-3-yl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

8-Azaguanine was persilylated first using the procedure described for the preparation of compound 9.9. Compound 9.8 (490 mg, 1.03 mmol) was dissolved in 20 mL anhydrous CH3CN, and treated with 10 mL CH3CN solution of persilylated 8-azaguanine base (392.9 mg, 1.03 mmol), followed by addition of SnCl4 (1M solution in CH2Cl2) (3 mL, 3 mmol). The mixture was stirred at r.t. for 24 h, cooled with ice-water and NaHCO3, filtered, and concentrated down under reduced pressure. The residue was subjected to a silica gel column eluting with 10% EtOH in EtOAc to give compound 10.1 (430 mg, 83% yield).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated down under reduced pressure
  3. washeluting with 10% EtOH in EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-7ddd4237a31344f5b3e40c33811b4a92
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324179B2

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