Potassium Acetate → HCID 66611486, Verbindung

HRID 1621453

Reaktionsgleichung

Reaktionsgleichung von HRID 1621453
Cl[C:2]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[O:18]1[CH2:22][CH2:21][O:20][CH:19]1[C:23]1[CH:24]=[C:25](B(O)O)[C:26]([F:29])=[N:27][CH:28]=1.C([O-])(=O)C.[K+]>CCO.C(P([Pd](P(C1C=CC(N(C)C)=CC=1)(C(C)(C)C)C(C)(C)C)(Cl)Cl)(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C>[O:18]1[CH2:22][CH2:21][O:20][CH:19]1[C:23]1[CH:24]=[C:25]([C:2]2[N:10]=[C:9]([CH3:11])[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[C:26]([F:29])=[N:27][CH:28]=1

Komponenten

6

Edukt 3

HCID 517044Potassium AcetateHCID 595482686-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 595483675-(1,3-Dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid

Produkt 1

HCID 66611486HCID 66611486, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178482906HCID 178482906, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

6-Chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (3.200 g, 12.66 mmol), 5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid (3.165 g, 14.86 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphino)dichloropalladium (514.9 mg, 0.7272 mmol), and potassium acetate (4.180 g, 42.59 mmol) were suspended in EtOH (50 mL) and water (10 mL) and nitrogen was bubbled through the suspension for about 15 seconds. Then, the flask was fitted with a reflux condenser and placed in a preheated oil bath (80° C.), and stirred under nitrogen for 1 hour. The reaction was cooled to room temperature, poured into water (125 mL), and extracted with DCM. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter (600 mL fritted filter with about 3 inches of silica gel, 40:1 DCM/2N ammonia in MeOH). The fractions with product were collected, concentrated, and washed repeatedly with hexanes and dried to give 6-(5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-yl)-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (4.557 g), which was used for the next step. MS (ESI pos. ion) m/z 386 (M+H)+.

Aufarbeitung

  1. customwater (10 mL) and nitrogen was bubbled through the suspension for about 15 seconds
  2. customThen, the flask was fitted with a reflux condenser
  3. customplaced in a preheated oil bath
  4. temperatureThe reaction was cooled to room temperature
  5. additionpoured into water (125 mL)
  6. extractionextracted with DCM
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified on a silica gel
  11. filtrationfilter (600 mL fritted filter with about 3 inches of silica gel, 40:1 DCM/2N ammonia in MeOH)
  12. customThe fractions with product were collected
  13. concentrationconcentrated
  14. washwashed repeatedly with hexanes
  15. customdried

Quellen und Nachweise

ORD-Eintrag
ord-57380d7b9b594c1f869e802df09f437a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

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