Reaktion #60830

Reaktionsgleichung

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

pyridine-4-boronic acid

sodium carbonate

EtOAc

→

title compound

Ausbeute 31.0%

2-(1-Methyl-4-phenyl-2-pyridin-4-yl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

Ausbeute 31.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthen washed with water (15 mL), brine (2×10 mL)
2. 2
   Trocknendried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigePurification by flash chromatography on silica eluting with 6% MeOH/DCM
6. 6
   Sonstigegave a dark brown solid which
7. 7
   Waschenwas washed with diethyl ether
8. 8
   Sonstigethen dried under high vacuum

Vorschrift

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Example 26) (20 mg), PdCl2dppf (8 mg), pyridine-4-boronic acid (8 mg) and 2M sodium carbonate (2.0 mL) were heated in DMF (2.0 mL) at 100° C. under an inert atmosphere. After 3 hours the reaction mixture was cooled to ambient temperature, EtOAc (25 mL) added then washed with water (15 mL), brine (2×10 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 6% MeOH/DCM gave a dark brown solid which was washed with diethyl ether then dried under high vacuum to give the title compound as light brown solid (6 mg, 31%);

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