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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 45026Erstellt: 24. Oktober 2026

Dichloromethane → 3-phenyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propan-1-ol

https://huagongshe.com/de/reaction/45026

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDichloromethaneHCID 6344—
EduktDiisobutylaluminumhydrideHCID 21225700—
Eduktmethyl 3-phenyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-propanoateHCID 57477997—
LösungsmittelHexaneHCID 8058—
Produkt3-phenyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propan-1-olHCID 5747799893,3%

Reaktionsbedingungen

Temperatur-78 °C

Reaktionsschritte

Diisobutylaluminum hydride in hexane (1 M, 0.69 mL) was added to a solution of methyl 3-phenyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-propanoate (150 mg, 0.00031 mol) in DCM (3 mL, 0.05 mol) and the mixture was cooled to −78° C. under a nitrogen atmosphere. The reaction was stirred for 1 h at −78° C. and was allowed to warm to room temperature for 4 hrs. The reaction was quenched with methanol (100 μL), and saturated ammonium chloride (100 μL), and then taken up in ethyl acetate dried over MgSO4 and filtered. The filtrate was concentrated to give 3-phenyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propan-1-ol (130 mg, 92%) as an oil. m/z=450 (M+1).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08541425B2
Quelldatensatzuspto-grants-2013_09
ORD IDord-066dd39be23b4c6db444d9483820fb25
Quellennotizuspto-grants-2013_09