Sodium hydride → 6-(4-Chloropyrimidin-2-ylthio)hexan-1-ol

6-Mercapto-1-hexanol (1.4 mL, 10.2 mmol) was added to a suspension of NaH (60% in mineral oil, 0.42 g, 10.5 mmol) in THF (20 mL) and stirred at room temperature for 10 min then cooled down to −78° C. in dry ice bath. A suspension of the product Example 46a (1.74 g, 9.03 mmol) was added to the above mixture and stirred at −78° C. for 2.5 hours. The reaction was quenched with water (20 mL) and extracted with Et2O (100 mL). The extract was washed with water (2×100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography eluting with 1:2 EtOAc:Hex to obtained the title compound as a viscous oil, 1.8 g (81%). 1H NMR (300 MHz, CDCl3) δ 8.67 (d, J=5.3 Hz, 1H), 7.00 (d, J=5.3 Hz, 1H), 3.63 (t, J=6.6 Hz, 2H), 3.14 (t, J=7.4 Hz, 2H), 2.60 (S, 1H), 1.8-1.4(mult, 8H); 13C NMR (75 MHz, CDCl3) δ 173.4, 160.7, 157.8, 116.2, 62.3, 32.3, 30.8, 28.6, 28.3, 25.1; mass spectrum (API-TIS) m/z 247 (M+H).

1. additionwas added to the above mixture
2. stirringstirred at −78° C. for 2.5 hours
3. customThe reaction was quenched with water (20 mL)
4. extractionextracted with Et2O (100 mL)
5. washThe extract was washed with water (2×100 mL) and brine (100 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe product was purified by silica gel column chromatography
10. washeluting with 1:2 EtOAc

ORD-Eintrag

ord-777c1c6b736c4214bc43d241b1ce20cb

Quelldatensatz

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06593347B2