反応 #331348

反応方程式

cis-toluene-4-sulfonic acid 3-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutylmethyl ester

dimethylamine

THF

→

title compound

7-(3-Dimethylamino methylcyclobutyl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

反応条件

後処理

1. 1
   その他The solvent was evaporated
2. 2
   workup.ADDITIONwater was added
3. 3
   抽出the mixture was extracted with CH2Cl2 (4×40 mL)
4. 4
   洗浄the extracts were washed with brine
5. 5
   乾燥dried over MgSO4
6. 6
   その他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
7. 7
   workup.ADDITIONcontaining product
8. 8
   その他dried in vacuo

実験手順

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).

出典