Sodium Carbonate → HCID 24905165, Verbindung

HRID 237988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237988
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8](B(O)O)[CH:7]=[CH:6][C:5]=12.I[C:14]1[C:22]2[C:17](=[N:18][CH:19]=[N:20][C:21]=2[NH2:23])[N:16]([CH:24]([CH3:26])[CH3:25])[N:15]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO.COCCOC.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>[N:3]1[O:2][N:1]=[C:5]2[CH:6]=[CH:7][C:8]([C:14]3[C:22]4[C:17](=[N:18][CH:19]=[N:20][C:21]=4[NH2:23])[N:16]([CH:24]([CH3:26])[CH3:25])[N:15]=3)=[CH:9][C:4]=12

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 4672597Benzo[C][1,2,5]Oxadiazole-5-Boronic AcidHCID 249053373-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Produkt 1

HCID 24905165HCID 24905165, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of Benzo[c][1,2,5]oxadiazole-5-boronic acid (18 mg, 0.11 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (30 mg, 0.10 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80° C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA44. ESI-MS (M+H)+ m/z calcd 296.1, found 296.1.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe reaction was extracted with saturated NaCl and CH2Cl2
  3. concentrationconcentrated in vacuo
  4. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)
  5. customto yield BA44

Quellen und Nachweise

ORD-Eintrag
ord-12ba751bef9543ac95e33d7e721f488b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642604B2

Notizen zur Reaktion

Wird geladen…