2,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide → 2,2,2-Trifluoro-n-propylacetamide

HRID 1825283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825283
[F:1][C:2]([F:10])([F:9])[C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4].[H][H]>[Pd]>[F:1][C:2]([F:10])([F:9])[C:3]([NH:5][CH2:6][CH2:7][CH3:8])=[O:4]

Komponenten

4

Edukt 2

HCID 110948052,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide2×HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 5809962,2,2-Trifluoro-n-propylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

In Reaction Scheme 4,6-amino-4-methoxypyrazolo[3,4-d]pyrimidine was converted to the iodo derivative (14) which was treated with 1-chloro-1,2-dideoxy-3,5-di-O-toluoylribofuranose to yield the nucleoside (15). Compound (15) was treated with NaOMe/MeOH to hydrolyze the toluoyl groups and yield the unblocked nucleoside (16). Treatment of (16) with aqueous sodium hydroxide gave (17) which could be converted to the trifluoro-N-prop-2-ynyl acetamide derivative (18). Compound (18) was reduced with hydrogen and a Pd catalyst to yield the trifluoro-N-propylacetamide derivative (19). The 4-amino group of compound (19) was protected by treatment with N,N-dimethylformamide dimethylacetal to give compound (20) which was converted to DMTr derivative (21) and then to the phosphoramidite derivative (22).

Quellen und Nachweise

ORD-Eintrag
ord-71d2f0ebb30540959490f06a3f38dfb8
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045610B2

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