Reaction #6439

Reaction equation

pyridine 3-carboxaldehyde

n-Butyllithium

4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidine

→

4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-α-(3- pyridinyl)- 2-pyrimidineethanol

Yield 50.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   Temperaturecooled to -78° C
2. 2
   workup.STIRRINGThe reaction mixture is stirred at room temperature for 3 hours
3. 3
   Otheris quenched by the addition of saturated aqueous ammonium chloride
4. 4
   ExtractionThe product is extracted into ether
5. 5
   DryingThe organic layer is dried (MgSO4)
6. 6
   Otherevaporated

Procedure

n-Butyllithium (1.5 mL of 1.6M solution in hexane, 2.4 mmol) is added dropwise to a solution of 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidine (750 mg, 2.4 mmol) in dry THF (12 mL) at 0° C. under an atmosphere of dry nitrogen. The reaction mixture is stirred at room temperature for 30 minutes and then cooled to -78° C. A solution of pyridine 3-carboxaldehyde (250 mg, 2.4 mmol) in dry THF (1 mL) is added dropwise. The reaction mixture is stirred at room temperature for 3 hours and then is quenched by the addition of saturated aqueous ammonium chloride. The product is extracted into ether. The organic layer is dried (MgSO4) and evaporated to give crude 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-α-(3- pyridinyl)- 2-pyrimidineethanol (500 mg, 50%) which is not further purified, but used directly in the next reaction.

Source