Triethylamine → 5-(4-Chloro-phenyl)-7-trifluoromethyl-3-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine

HRID 1293660Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][C:20](I)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24].CCN(CC)CC>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][C:20]([C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 23 °C

Versuchsvorschrift

A mixture of 5-(4-chloro-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (example C.4 step 2a and 2b) (13.96 g, 32.96 mmol), trimethylsilylacetylene (5.5 mL, 39.72 mmol) and Et3N (9.2 mL, 67.9 mmol) in dry DMF (33 mL) was stirred for 10 min at 23° C. while being purged with Argon, then PdCl2(PPh3)2 (116 mg, 0.5 mol %), PPh3 (43 mg, 0.5 mol %) and Cul (19 mg, 0.3 mol %) were added. Stirring was continued at 90° C. for 4 h. The react mixture was then cooled to 23° C., diluted with EtOAc, washed water (twice) and brine, dried over Na2SO4. Removal of the solvent left an orange solid (13.30 g, 102%). MS (ISP) 394.1 [(M+H)+] and 396.1 [(M+2+H)+]; mp 198° C.

Aufarbeitung

customwhile being purged with Argon
additionPdCl2(PPh3)2 (116 mg, 0.5 mol %), PPh3 (43 mg, 0.5 mol %) and Cul (19 mg, 0.3 mol %) were added
stirringStirring
waitwas continued at 90° C. for 4 h
temperatureThe react mixture was then cooled to 23° C.
additiondiluted with EtOAc
washwashed water (twice) and brine
dry with materialdried over Na2SO4
customRemoval of the solvent
waitleft an orange solid (13.30 g, 102%)

Quellen und Nachweise

ORD-Eintrag: ord-b94780f64300466fb064f000971e2801
Quelldatensatz: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07238808B2

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