Sodium Carbonate → 4-(5-Bromo-pyridin-3-yl)-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1878593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878593
I[C:2]1[C:3]2[CH:17]=[CH:16][NH:15][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)[N:7]=1.[Br:18][C:19]1[CH:20]=[N:21][CH:22]=[C:23](B(O)O)[CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.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>[Br:18][C:19]1[CH:24]=[C:23]([C:2]2[C:3]3[CH:17]=[CH:16][NH:15][C:4]=3[N:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=3)[N:7]=2)[CH:22]=[N:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 38148115-Bromopyridine-3-boronic acidHCID 866324294-iodo-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine2×

Produkt 1

HCID 441944484-(5-Bromo-pyridin-3-yl)-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 20074477Dimethoxyethane ethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-iodo-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (Intermediate 3) (1 eq, 1.50 mmol, 530 mg) and 3-bromopyridine-5-boronic acid (ABCR GmbH & Co. KG, Karlsruhe, Germany) (1.1. eq, 1.65 mmol, 339 mg) in DME/EtOH (1:1, 6 ml) are added aqueous Na2CO3 solution (2 M, 3 eq, 4.50 mmol, 2.2 ml) and Pd(PPh3)4 (0.05 eq, 0.075 mmol, 89 mg). The resulting mixture is heated using microwave radiation at 120° C. for 20 min. After cooling down to r.t., the mixture is filtered and the resulting precipitate is washed with EtOH. The residue is suspended in DCM, filtered, and dried to give the title compound; [M+H]+=366/368; 1H-NMR (400 MHz, DMSO): δ 12.58 (s, 1H), 9.40 (m, 1H), 8.89 (m, 1H), H), 8.79 (m, 1H), 8.37 (t, 1H), 7.87-7.77 (m, 2H), 7.33 (t, 1H), 7.00 (m, 1H), 2.56 (m, 3H).

Aufarbeitung

  1. temperatureThe resulting mixture is heated
  2. customat 120° C.
  3. customfor 20 min
  4. filtrationthe mixture is filtered
  5. washthe resulting precipitate is washed with EtOH
  6. filtrationfiltered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-278b8550318b4c3fbfcf06b277281765
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314112B2

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