Azido(trimethyl)stannane → HCID 178451517, Verbindung

HRID 602962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602962
[C:1]([C:3]1[N:4]=[CH:5][C:6]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][C:7]=2[N:8]=1)#[N:2].[N:19]([Sn](C)(C)C)=[N+:20]=[N-:21]>C1(C)C=CC=CC=1>[NH:19]1[C:1]([C:3]2[N:4]=[CH:5][C:6]3[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][C:7]=3[N:8]=2)=[N:2][N:21]=[N:20]1

Komponenten

4

Edukt 2

HCID 5104973Azido(trimethyl)stannaneHCID 184428191,1-Dimethylethyl 2-cyano-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate2×

Produkt 1

HCID 178451517HCID 178451517, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of tert-butyl 2-cyano-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (Intermediate 9, Step D) (71 mg, 0.29 mmol) in toluene was added azidotrimethyltin (596 mg, 2.9 mmol). The resulting mixture was heated at 110° C. overnight. After the solvent was removed under reduced pressure, the residue was purified by reverse-phase silica gel chromatography (gradient 5-50% acetonitrile in water containing 0.1% TFA) to yield tert-butyl 2-(1H-tetrazol-5-yl)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate. The product was treated as described for Intermediate 9, Step E, to yield the title compound.

Aufarbeitung

  1. customAfter the solvent was removed under reduced pressure
  2. customthe residue was purified by reverse-phase silica gel chromatography (gradient 5-50% acetonitrile in water containing 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-a2e4521f41304a8682bb751db6663fbc
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906649B2

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