Potassium Carbonate → 3-(3-benzyloxy-phenoxymethyl)-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 2426107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2426107
Br[CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[N:9][C:10]=2[Cl:12])[N:5]([CH3:13])[N:4]=1.[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([OH:28])[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=1)[O:28][CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[N:9][C:10]=2[Cl:12])[N:5]([CH3:13])[N:4]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 138048Benzyl 3-hydroxyphenyl etherHCID 575815813-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 575815893-(3-benzyloxy-phenoxymethyl)-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (90.2 mg, 0.28 mmol, Example 5), 3-benzyloxy-phenol (75.2 mg, 0.36 mmol, TCl) and potassium carbonate (59.6 mg, 0.43 mmol) in dimethylformamide was stirred at room temperature overnight. The resulting mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate, washed with water and brine, and dried and concentrated. The crude product was either used directly in the next step (described in Example 7) or purified by flash chromatography (silica gel, hexanes-ethyl acetate, 90/10 to 60/40) to give pure 3-(3-benzyloxy-phenoxymethyl)-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine. (Yield 33 mg).

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by flash chromatography (silica gel, hexanes-ethyl acetate, 90/10 to 60/40)

Quellen und Nachweise

ORD-Eintrag
ord-d70d398ada5249ec9c14f3f7715b420f
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968554B2

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