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19th March 2012 @ 00:07
This experiment is a repeat of JRC 8-1, with longer heating periods, to obtain a higher yield than was given in JRC 8-1. As with JRC 8-1, this experiment is based on one described by Son et al. (2011).


Reaction start time: 10am 14/03/2012
Methyl-3-aminothiophene-2-carboxyate (0.301 g, 1.91 mmol, 1 equiv.) was dissolved in formamide (1 mL, 25 mmol, ~25 equiv.) and stirred at 180°C for eight hr, followed by stirring at rt for 18 hr. The reaction mixture was extracted with ethyl acetate (2 x 20 mL), before being washed with water (2 x 20 mL) and brine (20 mL). Solvent was removed in vacuo to yield 0.086 g product. This crude product was purified by column chromatography using 10% EtOAc/hexane as an eluent. Results as follows:

DCM (used to dissolve the crude product) went through the column. Yield = 0.010 g
Fraction 1. Yield = 0.043 g
Fraction 2. Yield = 0.001 g

The remainder of the fractions were combined and the solvent reduced under pressure to yield 0.05 g of material

Risk Assessment:
As for JRC 8-1

Son, J.B.; Jung, S. H.; Choi, W.I.; Jung, Y.H.; Choi, J.Y.; Song, J.Y.; Lee, K.H.; Lee, J.C.; Kim, E.Y.; Ahn, Y.G.; Kim, M.S.; Choi, HG.; Sim, T.B.; Ham, Y.J.; Park, D.; Kim, H.; Kim, D. (Hanmi Holdings Co., Ltd., S. Korea; Korea Institute of Science and Technology; Catholic University Industry Academic Cooperation Foundation). Preparation of thienopyrimidine derivatives for use as protein kinase inhibitors. World Intellectual Property Organisation 2011093684 A2, 2011; SciFinder Scholar AN 2011:971406 (accessed 3/2/2012).
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