تفاعل #79888
ord-d74a51b4a91e47d69911f3e711c6116b
معادلة التفاعل
المتفاعلات
ظروف التفاعل
المعالجة
- 1أخرىA precipitate formed after 20 minutes
- 2أخرىReaction
- 3درجة الحرارةto cool to room temperature
- 4أخرىthe organic solvent was removed under reduced pressure
- 5أخرىThe product was partitioned between the aqueous sodium carbonate layer and ethyl acetate
- 6استخلاصThe aqueous layer was further extracted with ethyl acetate three times
- 7غسيلwashed with water and brine
- 8تجفيفdried over magnesium sulfate
- 9تركيزpartially concentrated until a precipitate
- 10أخرىformed
- 11ترشيحThe solid was filtered
- 12غسيلwashed with ethyl acetate
- 13أخرىdried under a high vacuum
الإجراء التجريبي
A mixture of 4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 7.15 mmol) in ethylene glycol dimethyl ether (100 mL) was treated with 4-(benzyloxy)phenylboronic acid (1.79 g, 7.87 mmol), tetrakis(triphenylphosphine)palladium (0.496 g, 0.429 mmol), and a solution of sodium carbonate (1.83 g, 17.16 mmol) in water (50 mL). A precipitate formed after 20 minutes. Reaction was stirred for 5 hours at 80° C. under a nitrogen atmosphere. The mixture was allowed to cool to room temperature and the organic solvent was removed under reduced pressure. The product was partitioned between the aqueous sodium carbonate layer and ethyl acetate. The aqueous layer was further extracted with ethyl acetate three times. The organic layers were combined, washed with water and brine, dried over magnesium sulfate, and partially concentrated until a precipitate formed. The solid was filtered, washed with ethyl acetate, and dried under a high vacuum. Yielded 2.06 g (61%) of 5-[4-(benzyloxy)phenyl]-4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidine. 1H NMR (DMSO-d6, 400 MHz) δ 8.64(s, 1H), 7.88(s, 1H), 7.52-7.33(m, 7H), 7.08-7.05(d, 2H, J=12 Hz), 5.15(s, 2H), 4.82-4.78 (m, 1H), 3.95-3.89(m, 4H), 2.21-2.13(m, 2H), 1.98-1.96(m, 2H), 1.85-1.75(m, 4H); Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt 8.356 min.