2,4-Dichloropyrimidine-5-carbaldehyde → 1-(2,4-Dichloropyrimidin-5-yl)ethan-1-ol
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customthe reaction was quenched with 1N HCl (10 mL)
- extractionThe resulting mixture was extracted with EtOAc
- dry with materialthe extract was dried with sodium sulfate
- customRemoval of solvent
- 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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