Acetone → HCID 117820822, compound

HRID 59098Notes

Reaction equation

HRID 59098 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[C:4]([CH2:10][O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[N:3]=1.[BH4-].[Na+].CC(C)=O.C(Cl)(Cl)Cl>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([CH2:10][O:11][CH2:12][C:13]([F:16])([F:14])[F:15])[N:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 1178209202-Chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde

Product 1

HCID 117820822HCID 117820822, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde (0.6 g, 2.36 mmol) was dissolved in ethanol (20 mL). Sodium borohydride (0.134 g, 3.54 mmol) was added and the mixture was stirred at rt for 10 min. Acetone (5 mL) was added and mixture was stirred for 10 min. Chloroform (20 mL) was added and the mixture was filtered through a pad of silica. The solvents were evaporated and the residue was purified by column chromatography on silica eluting with a gradient of methanol in DCM to give the title compound 0.35 g (58%).

Workup

  1. stirringmixture was stirred for 10 min
  2. filtrationthe mixture was filtered through a pad of silica
  3. customThe solvents were evaporated
  4. customthe residue was purified by column chromatography on silica eluting with a gradient of methanol in DCM

Sources & evidence

ORD record
ord-3d7f4b35b73644eea71b2d7c7e92a7a8
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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