2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 67358352, compound

Temperature

90 °C

(4-Oxo-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-7-yl)acetate (5 g, 17.10 mmol, from step 2) was added to DDQ (9.71 g, 42.76 mmol, 2.5 equiv) in 1,4-dioxane (50 mL) solution under argon. The reaction mixture was heated to 90° C. for 15 h. The mixture was then allowed to cool to rt and the brown solid precipitated from solution. The solid was filtered and washed with 1,4-dioxane (2×30 mL). The filtrate was concentrated in vacuo. Saturated aqueous NaHCO3 (150 mL) was then slowly poured into the concentrated filtrate at 0° C. The mixture was stirred at 0° C. for 10 min then extracted with DCM (3×300 mL). The combined organic layer was washed with saturated aqueous NaHCO3 (100 mL), brine (30 mL) and dried (Na2SO4), then concentrated in vacuo. Ethyl ether (2×15 mL) was used to triturated the product. After drying, 1.78 g (6.18 mmol, 35%) of the desired product was obtained as a brown solid and it was used without further purification. 1H-NMR (CD3OD) δ 8.46 (d, J=8.1 Hz, 1H), 8.18 (s, 1H), 7.84 (s, 1H), 7.43 (d, J=8.2 Hz, 1H), 4.14 (q, 2H), 3.79 (s, 2H), 1.25 (t, 3H), LCMS RT=2.52 min, [M+H]+=289

1. temperatureto cool to rt
2. customthe brown solid precipitated from solution
3. filtrationThe solid was filtered
4. washwashed with 1,4-dioxane (2×30 mL)
5. concentrationThe filtrate was concentrated in vacuo
6. additionSaturated aqueous NaHCO3 (150 mL) was then slowly poured into the concentrated filtrate at 0° C
7. extractionthen extracted with DCM (3×300 mL)
8. washThe combined organic layer was washed with saturated aqueous NaHCO3 (100 mL), brine (30 mL)
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated in vacuo
11. customto triturated the product
12. customAfter drying

ORD record

ord-b68fdbdb72134bae904b85e2d5a31315

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07750017B2