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11th March 2013 @ 04:47
Mnr: MNR81-90

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

As for Synthesis of thienopyrimidine MNR89-1

Hazard Assessment

HIRAC MNR89.pdf

Procedure

To methyl-3-aminothiophene-2-carboxylate (11.25 g, 71.6 mmol) and ammonium formate (4.96 g,  78.7 mmol) was added formic acid (2.97 mL, 78.73 mmol) and formamide (15.6 mL, 393 mmol) and the mixture was heated to 140 °C.  After 15 hours the reaction was cooled to room temperature and a solid formed.  This was washed with watyer and filtered to give an off white solid.   The crude was recrystalised with EtOH (400 ml) to give fine white crystals.

 

1st crop - 4.615 g, 30.3 mmol, 42%

2nd crop - 1.108 g, 7.3 mmol, 10 %

The ethanol was then concentrated to give - 3.15 g, 20.7 mmol, 29%

 

Total recovered - 8.873 g, 58.3 mmol, 81%

 

NMR

mnr89-2_1stcrop_1H.pdf
mnr89-2_crop1.zip

mnr89-2_3rdcrop_1H.pdf
mnr89-2_3rd_crop.zip
2nd crop and concentrated filtrated together - just as clean as the 1st crop

Conclusion

The concentrated filtrate was as clean as the recrystalisation therefore this step was not required unlike in MNR89-1.  In future attempts an NMR of the crude should be taken to judge if a recrystalisatin is required or not.

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
MNR89-2_table.PNG
mnr89-2_3rdcrop_1H.pdf
mnr89-2_1stcrop_1H.pdf
mnr89-2_crop1.zip
mnr89-2_3rd_crop.zip