Sodium borohydride → HCID 22563217, compound

HRID 23697Notes

Reaction equation

HRID 23697 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].[BH4-].[Na+]>C(O)C>[Cl:1][CH2:2][CH:3]([C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[OH:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22563232HCID 22563232, compound

Product 1

HCID 22563217HCID 22563217, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-1-pyrimidin-2-ylethanone (6.15 g, 39.3 mmol) was dissolved in ethanol (125 ml) and CeCl3.7H2O (14.64 g, 39.3 mmol) was added. Stirring was continued for 10 min then sodium borohydride (1.49 g, 39.3 mmol) was added over 2 min. After 1 hr the solid was filtered and the filtrate evaporated. Sat. ammonium chloride solution (25 ml) was added followed by brine (250 ml) and the mixture adjusted to pH3-4 with 1N.HCl. Extraction with ethyl acetate (3×250 ml) afforded an amber oil which was chromatographed over silica gel (150 g) to give the product as a pale yellow oil (3.85 g) Physical characteristics are as follows: Anal. Found: C, 45.08; H, 4.47; N, 17.46.

Workup

  1. filtrationAfter 1 hr the solid was filtered
  2. customthe filtrate evaporated
  3. additionSat. ammonium chloride solution (25 ml) was added
  4. extractionExtraction with ethyl acetate (3×250 ml)
  5. customafforded an amber oil which
  6. customwas chromatographed over silica gel (150 g)

Sources & evidence

ORD record
ord-4d3e142080e84e17bc3d62af9ebbfbf6
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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