Sodium borohydride → [5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-methanol

HRID 1293676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1293676
C([O:3][C:4]([C:6]1[N:11]2[N:12]=[CH:13][CH:14]=[C:10]2[N:9]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:7]=1)=O)C.[BH4-].[Na+]>CO.O1CCCC1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:8]2[CH:7]=[C:6]([CH2:4][OH:3])[N:11]3[N:12]=[CH:13][CH:14]=[C:10]3[N:9]=2)=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 670011225-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-7-carboxylic acid ethyl ester

Produkt 1

HCID 67000889[5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-methanolAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-7-carboxylic acid ethyl ester (60 mg, 0.2 mmol) in MeOH/tetrahydrofuran (1:1 v/v, 1 mL) was added at 0° C. over 5 min sodium borohydride (75 mg, 2.0 mmol). The mixture was stirred at 0° C. for 1 h and then poured into ice-cold 3 N HCl (3 mL). The mixture was extracted with AcOEt and the organic layer was washed with H2O, dried (Na2SO4), and evaporated in vacuo. The residue was chromatographed on silica gel using AcOEt/cyclohexane (1:2 v/v) as eluent to give [5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-methanol (45 mg, 87%). Pale yellow solid. MS (ISN) 258.1 [(M−H)−]; mp 185–186° C.

Aufarbeitung

  1. extractionThe mixture was extracted with AcOEt
  2. washthe organic layer was washed with H2O
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8622e2508836493f96263652a57aec17
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238808B2

Notizen zur Reaktion

Wird geladen…