All Notebooks | Help | Support | About
10th October 2013 @ 02:33

AEW 58-1 Scheme

Procedure:

MNR 99-3 (500 mg, 2.93 mmol, 1 equiv.) was dissolved in N,N-dimethylethylenediamine (1.91 mL, 17.7 mmol, 6 equiv.). The reaction mixture effervesced and all SM dissolved. TLC showed presence of SM and the mixture began to ppt out so it was stirred at 100 ˚C according to previous procedure.

After 1 h, no SM present on TLC although product couldn't be clearly seen either. Reaction mixture had turned from yellow solution to white/yellow cloudy mixture. Reaction was stopped and cooled to room temperature then partitioned between EtOAc and water. The aqueous phases were extracted with EtOAc (very cloudy white ppt started to form), then combined org. phases washed with brine, dried (MgSO4), filtered and evaporated to yield an orange oil.

AFter 1 h, no SM present on TLC although product couldn't be clearly seen either. Reaction mixture has turned from orange solution to white/yellow cloudy mixture. Reaction was stopped and cooled to room temperature then partitioned between EtOAc and water. The aqueous phases were extracted with EtOAc (insoluble white oil/solid started to crash out so all layers kept) then combined org. phases washed with brine, dried (MgSO4), filtered and evaporated to yield an orange oil, which slowly crystallised to an orange semi-solid (323 mg, 1.47 mmol, 83% crude yield) and used as crude in AEW 66-1. NMR shows impurity with similar signals to product - used without purification.

Data:

AEW 58-2 (100% EtOAc) just after mix at rt.jpg

Hazard and Risk Assessment:

See Synthesis of N1,N1-dimethyl-N2-(thieno[3,2-d]pyrimidin-4-yl)ethane-1,2-diamine (AEW 58-1)

InChi:

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

and

InChI=1S/C4H12N2/c1-6(2)4-3-5/h3-5H2,1-2H3

to 

InChI=1S/C10H14N4S/c1-14(2)5-4-11-10-9-8(3-6-15-9)12-7-13-10/h3,6-7H,4-5H2,1-2H3,(H,11,12,13)

Attached Files
AEW 58-2 (100% EtOAc) just after mix at rt.jpg
AEW 58-2 (100% EtOAc) just after mix at rt.jpg