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20th November 2017 @ 21:21

This reaction is the second attempt at preparing an analogue of pyrimethamine, following the method used for SGS 16-4.

Synthesis of SGS17-8-1

Deep purple crude 3-isobutoxy-2-(4-(trifluoromethyl)phenyl)pent-2-enenitrile (SGS17-5-1, ~1.7 g, 5.6 mmol, mixture of E and Z isomers) was dissolved in 20 mL DMSO.  Guanidine hydrochloride (1.173 g, 12.28 mmol) was added to the solution along with sodium methoxide (1.530g, 28.32 mmol), and then the mixure was heated at 80 oC for 40 h. After this time the reaction mixture turned a dark red. 

Reaction was worked up with addition of 30 mL of water, and then extracted with DCM (2 x 40 mL). Intense colour of reaction mixture made extraction difficult. 

TLC of SGS17-8-1 against SGS17-5-1 in isobutanol

TLC of CP SGS17-8-1 Against SM SGS17-5-1 in Isobutanol 

In the reaction mixture, the spot at Rf = 0.9 is orange in colour, and the spot at R= 0.6 appears colourless. In the starting material the spot 0.6 appears orange coloured and