Cyclopentanecarbaldehyde → HCID 59812873, compound

Temperature

-78 °C

4,6-Dichloro-2-methylsulfanyl-pyrimidine (8.0 g, 41.01 mmol) was dissolved in 500 mL dry THF and cooled to −78° C. Lithium diisopropylamine (36.9 mL of 2.0 M solution in hexanes) was added dropwise, and the reaction mixture was stirred for 20 minutes at −78° C. Cyclopentane-carboxaldehyde (8.05 g, 82.02 mmol was added, and the reaction mixture was stirred for 45 minutes at −78° C. The reaction was quenched by addition of saturated aqueous ammonium chloride. The aqueous mixture was extracted with ethyl acetate, and the combined organic layers were washed with water, washed with brine, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography (5% to 40% EtOAc in hexanes) to yield 9.76 g of cyclopentyl-(4,6-dichloro-2-methylsulfanyl-pyrimidin-5-yl)-methanol. Mass Spec. M+H=294.

1. stirringthe reaction mixture was stirred for 45 minutes at −78° C
2. customThe reaction was quenched by addition of saturated aqueous ammonium chloride
3. extractionThe aqueous mixture was extracted with ethyl acetate
4. washthe combined organic layers were washed with water
5. washwashed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated under reduced pressure
9. customThe residue was purified by flash chromatography (5% to 40% EtOAc in hexanes)

ORD record

ord-1ff3a68ed3f842b58b6c48af9a2645d7

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566708B2