(2-(Sec-butylamino)thiazolo[5,4-b]pyridin-5-yl)methanol → 2-(Sec-butylamino)thiazolo[5,4-b]pyridine-5-carbaldehyde

HRID 1671812Notes

Reaction equation

HRID 1671812 reaction equation
[CH:1]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([CH2:15][OH:16])[N:9]=2)([CH2:3][CH3:4])[CH3:2]>C1COCC1.O=[Mn]=O>[CH:1]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([CH:15]=[O:16])[N:9]=2)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 86257065(2-(Sec-butylamino)thiazolo[5,4-b]pyridin-5-yl)methanol

Product 1

HCID 575272422-(Sec-butylamino)thiazolo[5,4-b]pyridine-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-(sec-butylamino)thiazolo[5,4-b]pyridin-5-yl)methanol (0.1155 g, 0.487 mmol, 1.0 eq.) in THF (3.5 mL) under nitrogen was added MnO2 (0.6357 g, 7.3 mmol, 15.0 eq.). After 1 hr, the reaction solution was filtered through Celite and rinsed with THF. The filtrate was concentrated in vacuo to give crude 2-(sec-butylamino)thiazolo[5,4-b]pyridine-5-carbaldehyde as a colorless oil which was carried to the next step without 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-883bd289e4c14898a934f7635cce4607
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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