反应详情

A mixture of cis-toluene-4-sulfonic acid 3-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutylmethyl ester (1.50 g, 3.01 mmol) and a 2M solution of dimethylamine in THF (30 mL, 60 mmol) was heated to 55° C. for 23 h in a glass pressure tube. The solvent was evaporated, water was added, the mixture was extracted with CH2Cl2 (4×40 mL), and the extracts were washed with brine and dried over MgSO4. The crude material was chromatographed on silica gel [Jones Flashmaster, 10 g/70 mL cartridge, eluting with CH2Cl2 (1-8)→5% MeOH in CH2Cl2 (9-24)-10% MeOH in CH2Cl2 (25-35)-10% MeOH in CH2Cl2 with 0.07M NH3 (36-48)], fractions containing product were combined and dried in vacuo. One obtained the title compound as brown solid. 1H NMR (CDCl3, 400 MHz): δ=2.01-2.11 (mc, 2H), 2.26 (s, 6H), 2.30-2.43 (mc, 1H), 2.46 (d, J=6.8 Hz, 2H), 2.69-2.77 (m, 2H), 5.05-5.15 (m, 1H), 5.59 (brs, 2H), 7.20 (s, 1H), 8.26 (s, 1H). MS (ES+): m/z 372.1 (20) [MH+]. HPLC: tR=1.3 min (OpenLynx, polar—5 min).

1. customThe solvent was evaporated
2. additionwater was added
3. extractionthe mixture was extracted with CH2Cl2 (4×40 mL)
4. washthe extracts were washed with brine
5. dry with materialdried over MgSO4
6. customThe crude material was chromatographed on silica gel [Jones Flashmaster, 10 g/70 mL cartridge, eluting with CH2Cl2 (1-8)→5% MeOH in CH2Cl2 (9-24)-10% MeOH in CH2Cl2 (25-35)-10% MeOH in CH2Cl2 with 0.07M NH3 (36-48)], fractions
7. additioncontaining product
8. customdried in vacuo