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17th August 2016 @ 04:47

 

Repeat and scale-up of AEW 281-1 Synthesis of 5-(2-phenyl-2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)-3-(pyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyrazine (AEW 281-1)

Crude AEW 266-2 (~24.1, 1 equiv. mmol) was dissolved in anhyd. CH2Cl2 (120 mL) , PPTS was added (181 mg, 0.72 mmol, 0.03 equiv.) and the reaction mixture was cooled to 0 ˚C. 3,4-Dihydro-2H-pyran (0.99 mL, 28.9 mmol, 1.2 equiv.) was added and the reaction mixture stirred at 0 ˚C for 5 mins and then allowed to warm to rt and stirred overnight.

TLC faint but indicated reaction complete.

Ice water (80 mL) was added to quench the reaction and then organic layers were separated, aqueous layers extracted with CH2Cl2 (3 x 50 mL). Combined organic layers were washed with water (50 mL), brine (40 mL) and dried (MgSO4) filtered and evaporated to give pale orange oil in quantitative yield that was directly submitted to the next recduction reaction.

 

Data:

AEW 281-2.png
AEW 281-2.jcamp
AEW 281-2.mnova
AEW 281-2.zip

Strings

InChI=1S/C11H14O3/c1-2-14-11(13)10(8-12)9-6-4-3-5-7-9/h3-7,10,12H,2,8H2,1H3

to

InChI=1S/C16H22O4/c1-2-18-16(17)14(13-8-4-3-5-9-13)12-20-15-10-6-7-11-19-15/h3-5,8-9,14-15H,2,6-7,10-12H2,1H3

OCC(C(OCC)=O)C1=CC=CC=C1

to

O=C(OCC)C(COC1OCCCC1)C2=CC=CC=C2

Attached Files
AEW 181-2.png
AEW 181-2.rxn
AEW 181-2.cdxml
AEW 281-2.png
AEW 281-2.jcamp
AEW 281-2.mnova
AEW 281-2.zip