2-Methylpyrimidine-5-carbaldehyde → 1-(2-Methylpyrimidin-5-yl)ethanol

HRID 241864

Reaction equation

HRID 241864 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=1.[CH3:10][Mg]Br>O1CCCC1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:9])[CH3:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 31609702-Methylpyrimidine-5-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 547724471-(2-Methylpyrimidin-5-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-methylpyrimidine-5-carbaldehyde (5.00 g, 38.9 mmol) in tetrahydrofuran (85 mL) was slowly added 33 mL of 1.4 M methylmagnesium bromide solution in tetrahydrofuran at 0° C. The mixture was stirred at room temperature for 1 hour and then quenched with water (50 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (0-100% EtOAc/hexane) to afford a colorless oil.

Workup

  1. customat 0° C
  2. customquenched with water (50 mL)
  3. extractionextracted with EtOAc (3×200 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (0-100% EtOAc/hexane)
  7. customto afford a colorless oil

Sources & evidence

ORD record
ord-838c6debebd24135ba7330f32fb2be37
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Linked notes

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