تفاعل #1435757

معادلة التفاعل

NH4OH

MeOH

45

1-[[1,3-Bis(benzyloxy)-2-propoxy]methyl]-5-iodouracil

BCl3

→

title compound 46

المردود 65.0%

1-[[1,3-Dihydroxy-2-propoxy]methyl]-5-iodouracil

المردود 65.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.WAITat −60° C. for another 4 h
2. 2
   أخرىto quench
3. 3
   أخرىthe reaction
4. 4
   workup.STIRRINGAfter being stirred at room temperature for 1 h
5. 5
   تركيزthe mixture was concentrated in vacuo
6. 6
   أخرىThe residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (9:1 to 4:1)

الإجراء التجريبي

To a solution of 45 (1.90 g, 3.64 mmol) in anhydrous CH2Cl2 (60 mL) at −78° C. was added BCl3 (1 M solution in CH2Cl2, 30 mL, 30 mmol) dropwise. The mixture was stirred at −78° C. under nitrogen for 2 h, then at −60° C. for another 4 h. MeOH (10 mL) was added to quench the reaction, followed by 14% NH4OH solution to adjust the mixture to pH 7. After being stirred at room temperature for 1 h, the mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (9:1 to 4:1) to give the title compound 46 as a pale yellow solid (810 mg, 65%). 1NMR (DMSO-d6) δ 11.6 (s, 1H, NH), 8.19 (s, 1H, H-6), 7.20, 6.60 (2br, 2H, 2 OH), 5.15 (s, 2H, CH2N), 4.60 (m, 2H, CH2O), 3.53 (m, 1H, CHO), 3.41 (m, 2H, 2 CH2O).

المصدر