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23rd October 2013 @ 23:58

Attempt at synthesis of AT 6 without high pressure tube - more amenable to scale.

Didn't work - could try with isopropanol or stick to Althea's high pressure method.

NBProton of AT 6 recorded in MeOD, but in CDClooking for: 1H NMR (400 MHz, CDCl3): δ 7.40 (1H, s), 8.33 (1H, s).

Procedure:

Ammonia (28% w/v in H2O, 3 mL) was added to AT 5 (100 mg, 0.4 mmol), insoluble. The mixture was stirred at 100 ˚C for 48 h. Extracted into EtOAc, washed with water, brine, dried over MgSO4, filtered and evaporated to give a crude yellow solid - SM.

Data:

 

AEW 100-1 crude.pdf
AEW 100-1 crude.mnova
AEW 100-1.zip

Hazard and Risk Assessment:

See: Amination of bromochlorothienopyrimidine (AT-6-4) but without sealed tube or isopropanol.

InChi:

InChI=1S/C6H2BrClN2S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H

to 

InChI=1S/C6H4BrN3S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H,(H2,8,9,10)

Attached Files
AEW 100-1.png
AEW 100-1.cdxml
AEW 100-1 crude.pdf
AEW 100-1 crude.mnova
AEW 100-1.zip