2-((4-chloro-5-iodo-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide → 2-((4-chloro-5-(4-hydroxybut-1-ynyl)-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide

HRID 1984110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984110
[Cl:1][C:2]1[C:3]2[C:17](I)=[CH:16][N:15]([CH2:19][C:20]3[C:25]([CH3:26])=[C:24]([O:27][CH3:28])[C:23]([CH3:29])=[CH:22][N+:21]=3[O-:30])[C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]=1>C(O)CC#C>[Cl:1][C:2]1[C:3]2[C:17]([C:19]#[C:20][CH2:25][CH2:24][OH:27])=[CH:16][N:15]([CH2:19][C:20]3[C:25]([CH3:26])=[C:24]([O:27][CH3:28])[C:23]([CH3:29])=[CH:22][N+:21]=3[O-:30])[C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]=1

Komponenten

3

Edukt 1

HCID 866082292-((4-chloro-5-iodo-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide

Produkt 1

HCID 866082312-((4-chloro-5-(4-hydroxybut-1-ynyl)-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxideAusbeute 194,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 135663-Butyn-1-OLLösungsmittel

Versuchsvorschrift

Sonogashira coupling of 2-((4-chloro-5-iodo-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide (335 mg) with but-3-yn-1-ol (200 μL) according to the general procedure A gave crude 2-((4-chloro-5-(4-hydroxybut-1-ynyl)-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide (291 mg).

Quellen und Nachweise

ORD-Eintrag
ord-f42e68dc29894cbab38962becb798031
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544672B2

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