2-Chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde → HCID 121317230, compound

HRID 59075Notes

Reaction equation

HRID 59075 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Cl:6][C:7]1[N:12]=[C:11]([CH:13]=[O:14])[CH:10]=[C:9]([CH2:15][O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[N:8]=1>C(OCC)C>[Cl:6][C:7]1[N:12]=[C:11]([CH:13]([OH:14])[CH:1]([CH3:3])[CH3:2])[CH:10]=[C:9]([CH2:15][O:16][CH2:17][C:18]([F:21])([F:19])[F:20])[N:8]=1

Participants

4

Reactant 2

HCID 1178209202-Chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 121317230HCID 121317230, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Isopropyl magnesium chloride (0.601 mL, 2M solution, 1.20 mmol) was added dropwise to a solution of 2-chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde (180 mg, 0.71 mmol) in diethyl ether (10 mL) at −30° C. The mixture was quenched with a saturated aqueous solution of ammonium chloride and then extracted with ethyl acetate (×2). The combined organic phase was dried over sodium sulfate and concentrate. The residue was purified by column chromatography on silica to yield the title compound, 25 mg (12%).

Workup

  1. customThe mixture was quenched with a saturated aqueous solution of ammonium chloride
  2. extractionextracted with ethyl acetate (×2)
  3. dry with materialThe combined organic phase was dried over sodium sulfate
  4. concentrationconcentrate
  5. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-48f2c6215cd64e62b8ce6e2ecd9682a8
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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