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 colurnn 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 colurnn chromatography
10. washeluting with 1:2 EtOAc

ORDレコード

ord-78005fae46024ab498138f1f8b1886e1

出典データセット

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06297260B1