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24th February 2014 @ 01:04

Conclusions: The reaction was successful with a 43% yield of the pure product.

Resynthesis and upscale of JU 3-1 for use in JU 6-1 (link!).

Github Tag: Issue #158

Reaction Scheme

 

Procedure

Started 2:45pm 18/03/14

JU 2-2 (505 mg, 1.96 mmol) was stirred into CH2Cl2 (30 mL). PhI(OAc)2 (634 mg, 1.97 mmol) was added and the resulting solution was stirred at room temperature for 2.25 h. TLC analysis showed the reaction was near completion.

TLC JU 3-6 EtOAc:Hexane 50:50 2.25h.jpg

The reaction was left for a further 16 h. Examination by TLC showed the reaction was complete.

TLC JU 3-6 EtOAc:Hexane 50:50 end.jpg

The reaction mixture  was washed with 60 mL of saturated sodium hydrogen carbonate solution. The NaHCO3 layer was extracted with DCM (6 x 60 mL), dried over MgSO4 and filtered. The solvent was removed by rotary evaporation and dried in vacuo. The crude product was purified by flash column chromatography over silica. The column was first eluted with 50:50 EtOAc and Pet Benzine followed by 70:30 EtOAc:PB, 80:20 EtOAc:PB and 100% EtOAC. The pure product was a bright yellow solid (218 mg, 43% yield) and was analysed by 1H NMR as were the impure fractions (frac 63-88 and 89-94).

JU 3-6 pure DMSO 200 MHz 64 scans.pdf
JU 3-6 pure DMSO.zip

JU 3-6 frac 63-88 DMSO 200 MHz.pdf
JU 3-6 frac 63-88 DMSO.zip
JU 3-6 frac 89-94 DMSO 200MHz 64 scans.pdf
JU 3-6 frac 89-94.zip

13C NMR, pure, DMSO, 300 MHz

JU 3-6 pure 13C DMSO 300 MHz.pdf
JU 3-6 pure 13C.zip

 

HIRAC - see JU 3-1

InChI strings

InChI=1S/C12H8ClN5/c13-11-7-15-8-12(17-11)18-16-6-10-3-1-9(5-14)2-4-10/h1-4,6-8H,(H,17,18)/b16-6+

to

InChI=1S/C12H6ClN5/c13-10-6-15-7-11-16-17-12(18(10)11)9-3-1-8(5-14)2-4-9/h1-4,6-7H

SMILES

ClC1=CN=CC(N/N=C/C2=CC=C(C#N)C=C2)=N1

to

ClC1=CN=CC2=NN=C(C3=CC=C(C#N)C=C3)N21

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Attached Files
Reaction Scheme JU 3-1.png
TLC JU 3-6 EtOAc:Hexane 50:50 2.25h.jpg
TLC JU 3-6 EtOAc:Hexane 50:50 end.jpg
JU 3-6 pure DMSO 200 MHz 64 scans.pdf
JU 3-6 pure DMSO.zip
JU 3-6 pure 13C DMSO 300 MHz.pdf
JU 3-6 pure 13C.zip
JU 3-6 frac 63-88 DMSO 200 MHz.pdf
JU 3-6 frac 89-94 DMSO 200MHz 64 scans.pdf
JU 3-6 frac 63-88 DMSO.zip
JU 3-6 frac 89-94.zip