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

HRID 1452968Notes

Reaction equation

HRID 1452968 reaction equation
[CH:1]([NH:4][C:5]1[S:6][C:7]2[CH:12]=[C:11]([C:13](OC)=[O:14])[N:10]=[CH:9][C:8]=2[N:17]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O>C1COCC1>[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:17]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 57527243Thiazolo[4,5-c]pyridine-6-carboxylic acid,2-[(1-methylethyl)amino]-,methyl ester

Product 1

HCID 57527184(2-(Isopropylamino)thiazolo[4,5-c]pyridin-6-yl)methanolYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(isopropylamino)thiazolo[4,5-c]pyridine-6-carboxylate (0.1286 g, 0.51 mmol, 1.0 eq.) in THF (1.3 mL) under nitrogen at 0° C. was added LAH (1M, THF; 0.8 mL, 0.8 mmol, 1.6 eq.). After 1.25 h, ice and EtOAc were added, the cold bath was removed, and the solution was stirred to room temperature. The layers were separated, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give (2-(isopropylamino)thiazolo[4,5-c]pyridin-6-yl)methanol as a light yellow solid (0.1063 g, 93% yield).

Workup

  1. customthe cold bath was removed
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f36ef9c3c28e45959dd3d11599f03d92
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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