2,4-Dichloropyrimidine-5-carbaldehyde → 1-(2,4-Dichloropyrimidin-5-yl)ethan-1-ol

HRID 750484Notes

Reaction equation

HRID 750484 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=[O:10])=[CH:4][N:3]=1.[CH3:11][Mg]Br>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([OH:10])[CH3:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 189831682,4-Dichloropyrimidine-5-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 151416481-(2,4-Dichloropyrimidin-5-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 2,4-dichloro-pyrimidine-5-carbaldehyde (Example 17, 1.01 g, 5.7 mmol) in THF (10 mL), methyl magnesium bromide (Aldrich, 3 M in ether, 6.27 mmol, 2.1 mL) was added slowly at −78° C. The mixture was stirred for an additional 2 hours at −78° C. and the reaction was quenched with 1N HCl (10 mL). The resulting mixture was extracted with EtOAc and the extract was dried with sodium sulfate. Removal of solvent gave a brown solid. 1.07 g, 97%. MS (M+H)+, 193.

Workup

  1. customthe reaction was quenched with 1N HCl (10 mL)
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialthe extract was dried with sodium sulfate
  4. customRemoval of solvent
  5. customgave a brown solid

Sources & evidence

ORD record
ord-f0dabc8583a943b48fa5f0303b1eebc3
Source dataset
uspto-grants-2008_07
Patent number
US07405220B2

Reaction notes

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