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9th June 2014 @ 13:31

 

Synthesis of 6-Bromo-4-chlorothieno[3,2-d]pyrimidine (AEW 99-1) was repeated at 0.4x scale.

 

To the commercial starting material (0.84 g, 4.92 mmol, 1.0 equiv.) in THF (50 mL) at -78 C was added n-BuLi (4.6 mL, 7.4 mmol, 1.5 equiv.) dropwise and the reaction mixture stirred at -78 C for 30 minutes. Bromine (0.5 mL, 9.84 mmol, 2.0 equiv.) was added dropwise and the reaction mixture warmed to rt and stirred for 1 h. The reaction mixture was diluted with an aqueous solution of sodium thiosulfate (60 mL) and extracted into ethyl acetate (3 x 40 mL). The combined organic extracts were dried (MgSO4), concentrated under reduced pressure to give an orange solid (1.86 g) which contained the desired product with ca. 20% starting material by NMR. This was purified by dry column vacuum chromatography (10% ethyl acetate in heptane) to give a tan solid C1 (797 mg, 3.19 mmol, 64.8%) in acceptable purity by NMR.

 

NMR: 

PT-19-C1.pdf
Attached Files
PT-19-B1.pdf
PT-19-Starting Material.pdf
CJCOSDD_ptm19b1_100614_1H_av600.tar
CJCOSDD_ptm19sm_100614_1H_av600.tar
PT-19-C1.pdf
CJCOSDD_ptm19c1_100614_1H_av500.tar