(2-(Isopropylamino)thiazolo[4,5-c]pyridin-6-yl)methanol → 2-(Isopropylamino)thiazolo[4,5-c]pyridine-6-carbaldehyde

HRID 1671802Notes

Reaction equation

HRID 1671802 reaction equation
[CH:1]([NH:4][C:5]1[S:6][C:7]2[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[CH:9][C:8]=2[N:15]=1)([CH3:3])[CH3:2]>C1COCC1.O=[Mn]=O>[CH:1]([NH:4][C:5]1[S:6][C:7]2[CH:12]=[C:11]([CH:13]=[O:14])[N:10]=[CH:9][C:8]=2[N:15]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 57527184(2-(Isopropylamino)thiazolo[4,5-c]pyridin-6-yl)methanol

Product 1

HCID 575272142-(Isopropylamino)thiazolo[4,5-c]pyridine-6-carbaldehydeYield 162.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-(isopropylamino)thiazolo[4,5-c]pyridin-6-yl)methanol (0.1063 g, 0.476 mmol, 1.0 eq.) in THF (5 mL) under nitrogen was added MnO2 (0.6441 g, 7.4 mmol, 15.6 eq.). After 1.75 hr, the reaction solution was filtered through Celite and rinsed with THF. The filtrate was concentrated in vacuo to give crude 2-(isopropylamino)thiazolo[4,5-c]pyridine-6-carbaldehyde as a yellow solid (0.1711 g). This material was used without further purification.

Workup

  1. filtrationthe reaction solution was filtered through Celite
  2. washrinsed with THF
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b314ea6aeadf4522a939e66072715f2c
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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