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Water → 8-(1-Benzyl-1H-pyrazol-4-yl)-2-chloro-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

HRID 535983
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HRID 535983 반응식
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[NH:21][C:20]3[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17]([Cl:26])=[N:16][C:15]=3[N:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:33][Si:34]([CH2:37][CH2:38][O:39][CH2:40]Cl)([CH3:36])[CH3:35].O>CN(C=O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[N:21]([CH2:40][O:39][CH2:38][CH2:37][Si:34]([CH3:36])([CH3:35])[CH3:33])[C:20]3[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17]([Cl:26])=[N:16][C:15]=3[N:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 46913081HCID 46913081, 화합물

생성물 1

HCID 671348358-(1-Benzyl-1H-pyrazol-4-yl)-2-chloro-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one수율 25%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
0 °C

실험 절차

A mixture of 8-(1-benzyl-1H-pyrazol-4-yl)-2-chloro-1-propyl-1,7-dihydro-purin-6-one (0.9 g, 2.44 mmol), K2CO3 (1.01 g, 7.32 mmol) in DMF (10 ml) were cooled to 0° C. and added SEM-Cl (1.3 ml, 7.32 mmol). The reaction mixture was stirred at 25° C. for 20 hours. To this reaction mixture water (100 ml) was added and extracted with ethyl acetate (3×30 ml). The combined organic layer was washed with brine (30 ml) and dried over Na2SO4. The organic layer was evaporated to dryness and the crude product was purified by column chromatography using silica gel (100-200 mesh) and 10-15% ethyl acetate in hexane as an eluent to obtain 8-(1-Benzyl-1H-pyrazol-4-yl)-2-chloro-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.3 g, 25%) as a off white solid.

후처리

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. washThe combined organic layer was washed with brine (30 ml)
  3. dry with materialdried over Na2SO4
  4. customThe organic layer was evaporated to dryness
  5. customthe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-952c31e336dd4546a6dfdfd827a97f0f
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859566B2

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