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16th May 2013 @ 05:23

1.35 g, 4.11 mmol, 99% crude yield

Scheme AEW 53-1

Repeat of Nucleophilic Displacement of 4-chlorothienopyrimidine with Piperazine MNR107-1 to give MNR113-1 but using 1.5 equiv of amine rather than 2.

Procedure:

A mixture of MNR 99-4 (710 mg, 4.16 mmol, 1 equiv.) and MNR 107-1 (1.21 g, 6.24 mmol, 1.5 equiv) in EtOH (20 mL) was heated to reflux for 4 hours. Reaction complete by TLC. 

Reaction mixture was allowed to cool to room temperature and the resulting heterogeneous mixture was evaporated and then partitioned between EtOAc and a saturated solution of sodium hydrogen carbonate and then extracted with EtOAc, combined organic layers washed with brine, dried (MgSO4), filtered and evaporated to yield an off white solid (1.35 g, 4.11 mmol, 99% yield).

1H NMR (300 MHz, CDCl3) δ: 8.58 (1H, s), 7.71 (1H, d, J 5.5), 7.42 (1H, d, J 5.5), 7.37–7.23 (2H, m), 7.09–6.97 (2H, m), 4.04 (2H, t, J 4.9), 3.53 (2H, s), 2.58 (2H, t, J 4.9).

Data:

AEW 53-1 40% EtOAc in Hexane.png

AEW 53-1 crude 1H 200MHz.pdf

Hazard and Risk Assessment:

See: Nucleophilic Displacement of 4-chlorothienopyrimidine with Piperazine MNR107-1 to give MNR113-1

InChi

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

and

InChI=1S/C11H15FN2/c12-11-3-1-10(2-4-11)9-14-7-5-13-6-8-14/h1-4,13H,5-9H2

to

InChI=1S/C17H17FN4S/c18-14-3-1-13(2-4-14)11-21-6-8-22(9-7-21)17-16-15(5-10-23-16)19-12-20-17/h1-5,10,12H,6-9,11H2

Attached Files
AEW 53-1.png
AEW 53-1 crude 1H 200MHz.pdf
AEW 53-1 40% EtOAc in Hexane.png
AEW 53-1 40% EtOAc in Hexane.png