Ammonium Chloride → 3-((7-Chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile

HRID 2036963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036963
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[Br-].[C:13]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][Zn+])#[N:14].[NH4+].[Cl-]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[Cl:8][C:6]1[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=[C:2]([CH2:18][C:17]2[CH:16]=[C:15]([CH:22]=[CH:21][CH:20]=2)[C:13]#[N:14])[CH:7]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidineHCID 178509756HCID 178509756, Verbindung

Produkt 1

HCID 866546533-((7-Chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrileAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To the reaction flask, 5,7-dichloropyrazolo[1,5-a]pyrimidine (452 mg, 2.4 mmol) was added along with (3-cyanobenzyl)zinc(II) bromide (6 mL, 3.75 mmol, 0.625M in DMF), Pd(PPh3)4 (110 mg, 0.1 mmol), and DMF (10 mL). The reaction was heated at 60° C. for 4 hours then cooled to room temperature. The reaction mixture was poured into saturated aqueous NH4Cl solution and ice and extracted with ethyl acetate. The combined extracts were washed with water, saturated NaCl solution, and then dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography on silica using 35% ethyl acetate/hexanes as the eluent. The product, 347-chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was recovered in 64% yield. LCMS (M+1=269)

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water, saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography on silica using 35% ethyl acetate/hexanes as the eluent
  7. customThe product, 347-chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was recovered in 64% yield

Quellen und Nachweise

ORD-Eintrag
ord-6cf1797549dc42d9920814476654b213
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575177B2

Notizen zur Reaktion

Wird geladen…