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30th April 2013 @ 06:05
Mnr: mnr121-130

Starting material from commercially purchased 4-chloroethieno[3,2-d]pyrimidine

As for Nucleophilic Displacement of MNR99 with Morpholine to give MNR100-1

 

Hazard Assessment


Procedure

To 4-chloroethieno[3,2-d]pyrimidine (2.0 g, 11.72 mmol) was added dimethylamine in absolute alcohol (4.2 mL, 23.44 mmol) at room temperature.  The mixture gave off some white gas and was stirred.  The solid quickly went into solution then almost instantly as solid started to precipitate out of the mixture.  The mixture was not heated as planned and was left to stir for 20 minutes.  TLC after 20 minutes showed complete consumption of starting material and one new, lower running spot.  The mixture was concentrated and crude NMR showed what looked like product but with a 1:1 ratio of dimethylamine still present.

TLC


TLC 50% EtOAc/Hex 

2013-04-30 11.56.14.jpg

TLC 100% EtOAc

2013-04-30 12.07.53.jpg


Crude NMR

mnr122-1_crude_1H.pdf
mnr122-1_crude_13C.pdf
mnr122-1_crude.zip

 

The crude was dissolved in CHCl3 (25 mL) and washed with sodium hydrogen carbonate (20 mL) and then extracted with CHCl3 (25 mL x 2).  The organic layers were combined, dried, filtered and concentrated to give an off white/pale yellow solid (1.94 g, 10.82 mmol, 92%)

 

Workup NMR

mnr122-1_workup_1H.pdf
mnr122-1_workup_13C.pdf
mnr122-1_workup.zip

Conclusion

Product obtained clean and in high yeild after workup, no need for further purification.  Taken on to the next step MNR124-1

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Attached Files
MNR122_scheme.png
2013-04-30 11.56.14.jpg
2013-04-30 12.07.53.jpg
MNR122-1_table.PNG
mnr122-1_crude_13C.pdf
mnr122-1_crude_1H.pdf
mnr122-1_crude.zip
mnr122-1_workup_13C.pdf
mnr122-1_workup_1H.pdf
mnr122-1_workup.zip