All Notebooks | Help | Support | About
24th January 2013 @ 03:46
Mnr: MNR81-90

Synthesis of thienopyrimidine (MNR89-1) from methyl-3-aminothiophene-2-carboxylate

As for compound 22, Method B

Hazard Assessment

HIRAC MNR89.pdf

Procedure

To methyl-3-aminothiophene-2-carboxylate (9.89 g, 62.9 mmol) and ammonium formate (4.36 g, 69.2 mmol) was added formic acid (2.61 mL, 69.21 mmol) and formamide (13.7 mL, 346 mmol) and the mixture was heated to 140 °C.  After 19 hours, the reaction was cooled to room temperature, filtered and washed with water to give an off white solid that was dried under vacuum (7.5 g).  NMR of this showed desired product with slight traces of impurities.  The crude was recrystalised with EtOH (230 ml) to give fine white crystals.

 

1st crop - 3.075 g, 20.21 mmol, 32 %

2nd crop 3.94 g, 25.89 mmol, 41 %

Total recovered - 7.015 g, 46.1 mmol, 73 %

 

NMR

crude filter

 

mnr89-1_filter_1H.pdf
mnr89-1_filter.zip

1st crop

mnr89-1_1stcrop_1H.pdf
MNR89-1_1stCrop.zip


Strings


Starting Material

InChI=1S/C6H7NO2S/c1-9-6(8)5-4(7)2-3-10-5/h2-3H,7H2,1H3

InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)

Product

InChI=1S/C6H4N2OS/c9-6-5-4(1-2-10-5)7-3-8-6/h1-3H,(H,7,8,9)

Linked Posts
Attached Files
MNR89-1_table.PNG
MNR89_scheme.png
HIRAC MNR89.pdf
mnr89-1_1stcrop_1H.pdf
mnr89-1_filter.zip
MNR89-1_1stCrop.zip
mnr89-1_filter_1H.pdf