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17th May 2013 @ 10:07

Starting material from commercially purchased 4-chloroethieno[3,2-d]pyrimidine

Repeat of Nucleophilic Displacement of MNR99 with ethyl 1-piperazinecarboxylate to give MNR126-1 but with 1.5 equiv of amine rather than 2.

 

Scheme AEW 54-1

Procedure

To 4-chloroethieno[3,2-d]pyrimidine (1.0 g, 5.86 mmol, 1 equiv) in THF (7 mL) (ethanol (5 mL added to get the starting material into solution) was added ethyl 1-piperazinecarboxylate (1.29 mL, 8.79 mmol, 1.5 equiv) at 0 ˚C.  The reaction was stirred at room temperature overnight. Still some SM 20 h later. Stirred for the rest of the weekend. On Monday still SM but volatiles removed in vacuo (~4 mL remains) and then dissolved in EtOAc, washed with a saturated aqueous solution of sodium hydrogen carbonate, water, brine, dried (MgSO4), filtered and evaporated to give a cream solid (1.93g) containing ~1:<0.1 product:SM. Decided to column rather than use crude to avoid purification problems in the next step.

Hazard and Risk Assessment:

See Nucleophilic Displacement of MNR99 with ethyl 1-piperazinecarboxylate to give MNR126-1 and links contained within.

Data:

AEW 54 and 55 100% EtOAc.jpg

Crude 1H NMR

AEW54-1-crude.pdf
AEW 54-1.zip

InChi

InChI=1S/C6H3ClN2S/c7-6-5-4(1-2-10-5)8-3-9-6/h1-3H

and

InChI=1S/C7H14N2O2/c1-2-11-7(10)9-5-3-8-4-6-9/h8H,2-6H2,1H3

to give

InChI=1S/C13H16N4O2S/c1-2-19-13(18)17-6-4-16(5-7-17)12-11-10(3-8-20-11)14-9-15-12/h3,8-9H,2,4-7H2,1H3

Attached Files
AEW 54-1.png
AEW 54 and 55 100% EtOAc.jpg
AEW54-1-crude.pdf
AEW 54-1.zip