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5th July 2013 @ 01:13

Repeat of Synthesis of N-methylthieno[3,2-d]pyrimidin-4-amine (MJT 7-1) (amounts of SM doubled), nucleophilic aromatic substitution of chlorine for methylamine to bring through more material to allow repeat of Synthesis of 6-bromo-N-methylthieno[3,2-d]pyrimidin-4-amine (MJT 9-1) using more equivalents of BuLi in the hope of a better 

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Reaction completed in 97 % yield, product was pure after extraction. 200 mg of product taken forward in MJT 9-2.

This is a novel compound; data to be collected: IR, LRMS, HRMS


Procedure

Methylamine (24% w/v in H2O, 4.2 mL, 22 mmol, 6 equiv.) was added to MNR 99-3 (0.590 g, 3.46 mmol), insoluble. The mixture was heated to 100oC, MNR 99-3 dissolved to give a pale yellow solution, the heat was reduced to 85oC and maintained for 6 hours by which time the reaction was a slurry of white solid in yellow solution. TLC (EtOAc) showed reaction had gone to completion. The reaction mixture was cooled to room temperature before the reaction was worked up with water (20 mL) and the product was extracted with ethyl acetate (3 x 20 mL). The combined ethyl acetate extracts were washed with brine before drying over Na2SO4 and removal of solvent to give MJT 7-2 (0.552 g, 3.34 mmol, 97 %) as a white powder. NMR matched MJT 7-1 and showed product was pure.

Hazard and Risk Assessment

HIRAC MJT 7-1

Data

TLC 6h EtOAc

 

TLC 6h EtOAc.JPG

Characterisation Data

1H NMR

MJT_7-2_H.pdf
 
MJT 7-2 Proton NMR raw data

13C NMR

MJT_7-2 Carbon.pdf
 
MJT 7-2 Carbon NMR raw data

Mpt. 156-160 ˚C

Linked Posts
Attached Files
amounts table MJT 7-2.PNG
TLC 6h EtOAc.JPG
MJT 7-2.pdf
MJT 7-2 NMR pdf
MJT_7-2 Carbon.pdf
MJT_7-2_H.pdf
MJT 7-2 Carbon NMR raw data
MJT 7-2 Proton NMR raw data