Water → 1-(4,6-Dichloropyrimidin-5-yl)ethan-1-ol

HRID 1931584Notes

Reaction equation

HRID 1931584 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[C:10]([CH:11]=[O:12])=[C:9]([Cl:13])[N:8]=[CH:7][N:6]=1.O>O1CCCC1>[Cl:4][C:5]1[C:10]([CH:11]([OH:12])[CH3:1])=[C:9]([Cl:13])[N:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde2×HCID 178418573HCID 178418573, compound

Product 1

HCID 122782581-(4,6-Dichloropyrimidin-5-yl)ethan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylmagnesium bromide solution (1.4 M in toluene/tetrahydrofuran (75:25); 2.4 mL, 3.4 mmol) was added to a solution of 4,6-dichloro-pyrimidine-5-carbaldehyde (Intermediate 16; 500 mg, 2.8 mmol) in tetrahydrofuran at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 10 min and then at room temperature for 30 min. Water was added and the mixture was extracted with ethyl acetate (3×25 mL). The organic layers were washed with water and brine, dried (sodium sulfate), filtered, and evaporated to give 1-(4,6-dichloro-pyrimidin-5-yl)-ethanol (540 mg, 100%) which was used directly in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 1.19 (d, 3H, J=6.3 Hz), 2.62 (br s, 1H), 5.48-5.54 (m, 1H), 8.68 (s, 1H).

Workup

  1. waitat room temperature for 30 min
  2. extractionthe mixture was extracted with ethyl acetate (3×25 mL)
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b1ac7ead17744bbe9a95e1a5435b568e
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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