反応 #331349

反応方程式

NaHCO3

pyridine

cis-[3-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutyl]-methanol

Ts2O

→

title compound

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

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   その他the organic phase was separated
2. 2
   抽出The aqueous phase was extracted with CH2Cl2 (50 mL)
3. 3
   洗浄The combined organic phases were washed with H2O (2×100 mL) and brine (100 mL)
4. 4
   乾燥dried over MgSO4
5. 5
   その他After removing the solvent
6. 6
   その他a brown paste (2050 mg) was obtained
7. 7
   その他The brown paste was purified by chromatography on silica gel (50 g pre-packed column)
8. 8
   洗浄eluted with CH2Cl2 (600 mL), 2% MeOH/CH2Cl2 (600 mL), and 4% MeOH/CH2Cl2 (600 mL)

実験手順

Into the suspension of cis-[3-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutyl]-methanol (1322 mg, 3.842 mmol) in CH2Cl2 (55 mL) was added dropwise pyridine (6749 μL, 21.7 eq.) at −78° C. under N2 over 10 min followed by the addition of a solution of Ts2O (1568 mg, 1.25 eq.) in CH2Cl2 (35 mL) over 20 min. After stirring at rt for 3 h, the reaction mixture was treated with saturated NaHCO3, and the organic phase was separated. The aqueous phase was extracted with CH2Cl2 (50 mL). The combined organic phases were washed with H2O (2×100 mL) and brine (100 mL), and dried over MgSO4. After removing the solvent, a brown paste (2050 mg) was obtained. The brown paste was purified by chromatography on silica gel (50 g pre-packed column) and eluted with CH2Cl2 (600 mL), 2% MeOH/CH2Cl2 (600 mL), and 4% MeOH/CH2Cl2 (600 mL) to obtain the title compound as a light-brown foam. 1H NMR (CDCl3, 400 MHz): δ=2.20-2.28 (m, 2H), 2.47 (s, 3H), 2.47-2.52 (m, 1H), 2.57-2.64 (m, 2H), 4.12-4.13 (d, 2H, J=5.2 Hz), 5.07-5.11 (m, 1H), 5.63 (brs, 2H), 7.14 (s, 1H), 7.37-7.39 (d, 2H, J=7.6 Hz), 7.81-7.84 (m, 2H), 8.22 (s, 1H). MS (ES+): m/z 498.9 (100) [MH+]. HPLC: tR=3.0 min (OpenLynx, polar—5 min).

出典