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

HRID 594292Notes

Reaction equation

HRID 594292 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=2)[C:10](OC)=[O:11])[S:5][CH:6]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:8]=[C:9]([CH2:10][OH:11])[CH:14]=[CH:15][N:16]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69081774Methyl 2-(4-methylthiazol-2-yl)isonicotinate

Product 1

HCID 69083230(2-(4-Methylthiazol-2-yl)pyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-(4-methylthiazol-2-yl)isonicotinate (2.400 g; 10.20 mmol) in anh. MeOH (50 ml) was treated with NaBH4 (775 mg; 20.50 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 17 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-(4-methylthiazol-2-yl)pyridin-4-yl)methanol as a yellow solid. LC-MS (conditions A): tR=0.47 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-e38fbccbdcb4433198ef25c74d1a052e
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

Loading…