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 diusopropylamine (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-667c3876f5744eddb254407124f54811

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07435731B2