Sodium Carbonate → 5-Bromo-2-phenylpyrimidine

HRID 42277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42277
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 70066515-Bromo-2-iodopyrimidine

Produkt 1

HCID 143877455-Bromo-2-phenylpyrimidineAusbeute 110,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture consisting of 5-bromo-2-iodopyrimidine (Bridge Organics, 10.0 g, 35.1 mmol), benzene boronic acid (Alfa Aesar, 4.25 g, 35.1 mmol), tetrakis(triphenylphosphine)palladium (Strem, 0.405 g, 0.351 mmol), toluene (150 mL), and a 2 M aqueous sodium carbonate solution (35 mL) was stirred at 115° C. (degrees Celsius) under a nitrogen atmosphere for 16 hours. After cooling to room temperature, the mixture was partitioned between chloroform (250 mL) and brine (200 mL). The phases were separated and the organic phase was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an orange oil (9.1 g). The crude product was purified by flash silica column chromatography. Elution through a 500-g Analogix® flash silica cartridge with 100% hexanes afforded the title intermediate as a white solid (3.15 g, 38% yield). Rf 0.69 with 9:1 v/v hexanes-ethyl acetate; 1H-NMR (400 MHz; CDCl3) δ 8.83 (s, 2H), 8.44-8.38 (m, 2H), 7.52-7.46 (m, 3H); MS (APCI+) m/z 236.9 (M+1).

Aufarbeitung

  1. customthe mixture was partitioned between chloroform (250 mL) and brine (200 mL)
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1fc24fe514de4ee08c3f119e7ea34aac
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536185B2

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