Potassium Carbonate → 8-{4-[3-(4-Fluoro-Phenyl)-prop-2-ynyloxy]-phenyl}-1-propyl-2-(3-trifluoromethyl-phenyl)-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

HRID 536002노트

반응식

HRID 536002 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:15]3[C:14](=[O:25])[N:13]([CH2:26][CH2:27][CH3:28])[C:12]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=4)=[N:11][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:46][C:47]#[C:48][C:49]1[CH:54]=[CH:53][C:52]([F:55])=[CH:51][CH:50]=1>CC(C)=O>[F:55][C:52]1[CH:53]=[CH:54][C:49]([C:48]#[C:47][CH2:46][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:15]4[C:14](=[O:25])[N:13]([CH2:26][CH2:27][CH3:28])[C:12]([C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=5)=[N:11][C:10]=4[N:9]=3)=[CH:6][CH:7]=2)=[CH:50][CH:51]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 105605241-(3-Bromoprop-1-yn-1-yl)-4-fluorobenzeneHCID 1363910258-(4-Hydroxy-phenyl)-1-propyl-2-(3-trifluoromethyl-phenyl)-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

생성물 1

HCID 671334448-{4-[3-(4-Fluoro-Phenyl)-prop-2-ynyloxy]-phenyl}-1-propyl-2-(3-trifluoromethyl-phenyl)-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one수율 43%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
60 °C

실험 절차

A mixture of 8-(4-Hydroxy-phenyl)-1-propyl-2-(3-trifluoromethyl-phenyl)-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.115 g, 0.21 mmol), potassium carbonate (0.067 g, 0.48 mmol), 1-(3-bromo-prop-1-ynyl)-4-fluoro-benzene (0.67 g, 0.27 mmol) and acetone (10 ml) was heated at 60° C. for 2 hours. The mixture was cooled to room temperature and filtered through sintered funnel, washed with acetone. Solvent was evaporated and the residue was purified by preparative TLC to obtain pure 8-{4-[3-(4-Fluoro-Phenyl)-prop-2-ynyloxy]-phenyl}-1-propyl-2-(3-trifluoromethyl-phenyl)-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.061 g, 43%) as pale yellow oil.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through sintered funnel
  3. washwashed with acetone
  4. customSolvent was evaporated
  5. customthe residue was purified by preparative TLC

출처 및 근거

ORD 기록
ord-d99262d67d8a4fb482f618e47df0e2e8
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859566B2

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