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3rd July 2014 @ 10:38

 

 

Conditions from Synthesis of 3-(7-aminothiazolo[4,5-d]pyrimidin-2-yl)-4-methyl-benzenesulfonamide (PT-22) were used on a 2x scale, to synthesise OSM-S-106.

 

PT-21-B1 (56.7 mg, 0.2 mmol) was dissolved in isopropyl alcohol (4 mL) and to this was added PT-18-D1 (68 mg, 0.24 mmol, 1.2 eq) followed by potassium carbonate solution (1M, 0.4 mL, 2 equivalents). The solution was degassed with nitrogen for 5 minutes and Pd(dppf)2.CH2Cl2 (32 mg, 40 umol, 20 mol%) was added. The reaction was heated to 90°C for 30 minutes under microwave irradiation in a sealed vessel, then evaporated to dryness. NMR (B1) indicated peaks consistent with a single major product, the title compound, plus misc. impurities (Reference spectrum):

PT-23-B1 1H NMR detail.png

The crude mixture was purified by dry flash column chromatography (gradient: 100% chloroform to 80% chloroform, 18% methanol, 2% sat. aq. ammonia) to give the title compound in two batches: 

C1, pale tan solid, 32.3 mg, 0.105 mmol, 52.8%

C2, tan solid, 23.1 mg, 0.075 mmol, 37.7%

Combined yield: 90.5%


Attached Files
PT-23.png
PT-23-B1 1H NMR detail.png
CJCOSDD_ptm23b1meod_030714_1H-1H-1H_av600_JulIV-00084.tar