Sodium borohydride → (2-(5-Methylthiazol-2-yl)pyridin-4-yl)methanol

HRID 594295Notes

Reaction equation

HRID 594295 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=2)[C:10](OC)=[O:11])=[N:4][CH:3]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([CH2:10][OH:11])[CH:14]=[CH:15][N:16]=2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69082465Methyl 2-(5-methylthiazol-2-yl)isonicotinate

Product 1

HCID 69084104(2-(5-Methylthiazol-2-yl)pyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-(5-methylthiazol-2-yl)isonicotinate (2.390 g; 10.20 mmol) in anh. MeOH (50 ml) was treated with NaBH4 (772 mg; 20.40 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 24 h. After concentration to dryness under reduced pressure, the resulting residue was treated with water, and extracted with DCM. The organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded (2-(5-methylthiazol-2-yl)pyridin-4-yl)methanol as an off-white solid. LC-MS (conditions A): tR=0.48 min.; [M+H]+: 207.05 g/mol.

Workup

  1. concentrationAfter concentration to dryness under reduced pressure
  2. additionthe resulting residue was treated with water
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was then dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-86bc52013600493b9105320c39b6a968
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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