Reaction #1265383

Reaction equation

7a

{2-[2-(3,5-Dimethyl-phenylamino)-pyrimidin-4-yl]-thiazol-4-yl}-methanol

t-butanol

Dess_Martin periodinane

→

aldehyde

2-[2-(3,5-Dimethyl-phenylamino)-pyrimidin-4-yl]-thiazole-4-carbaldehyde

Solvents

DCM

Conditions

Workup

1. 1
   Otherwas quenched with sodium thiosulfate (1 mL)
2. 2
   workup.STIRRINGIt was stirred until the two phase
3. 3
   DryingThe organic layer was dried (Na2SO4)
4. 4
   Concentrationconcentrated in vacuo

Procedure

To a solution of 7a (100 mg, 0.320 mmol) and 163 uL of t-butanol in 2 mL of DCM was added 163 mg of Dess_Martin periodinane reagent. The reaction mixture was stirred for 1 h after which it was quenched with sodium thiosulfate (1 mL). It was stirred until the two phase became clear. The organic layer was dried (Na2SO4) and concentrated in vacuo to give 35 mg (38%) the crude aldehyde 9a that was used directly for the next step. 1H NMR (CDCl3) δ 10.1 (s, 1H), 8.3 (d, 1H), 8.1 (s, 1H), 7.5 (d, 1H), 7.2 (s, 2H), 6.8 (s, 1H), 2.3 (s, 6H).

Source