Ammonium Chloride → 2-methylThiazolo[5,4-b]pyridine-5-methanol

HRID 2259524Notes

Reaction equation

HRID 2259524 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:12])=[N:11][C:6]2=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].[NH4+].[Cl-]>CCO>[OH:2][CH2:1][C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:12])=[N:11][C:6]2=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 190029165-Formyl-2-methylthiazolo[5,4-b]pyridine

Product 1

HCID 190028842-methylThiazolo[5,4-b]pyridine-5-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of the product of Step 5 (3.733 g, 21 mmol) in 200 mL of EtOH at 0° C. was added NaBH4 (800 mg, 21 mmol) and the mixture was stirred at 0° C. for 5 min. Saturated aq. NH4Cl was then added slowly and the product was extracted in EtOAc:THF 1:1, dried over Na2SO4, and purified by flash chromatography on silica with acetone: toluene 30:70; yield: 3.49 g, (92%).

Workup

  1. extractionthe product was extracted in EtOAc:THF 1:1
  2. dry with materialdried over Na2SO4
  3. custompurified by flash chromatography on silica with acetone: toluene 30:70

Sources & evidence

ORD record
ord-679ce88d777444b9b7297603e5f321c8
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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