Potassium Carbonate → HCID 90402924, 화합물

HRID 2200705노트

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HRID 2200705 반응식
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[NH:14][C:13]([CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=4)=[N:12][C:11]=3[N:10]([CH3:33])[C:9]2=[O:34])=[CH:5][CH:4]=1.Br[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[Cl:45][C:42]1[CH:43]=[CH:44][C:39]([CH2:38][N:14]2[C:15]3[C:16](=[O:17])[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:36][CH:35]=4)[C:9](=[O:34])[N:10]([CH3:33])[C:11]=3[N:12]=[C:13]2[CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:31])([F:32])[F:30])[CH:23]=2)=[CH:40][CH:41]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 90403762HCID 90403762, 화합물2회

생성물 1

HCID 90402924HCID 90402924, 화합물수율 92.5%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of 1-(4-methoxybenzyl)-3-methyl-8-(3-(3-(trifluoromethoxy)phenoxy)propyl)-1H-purine-2,6(3H,7H)-dione (130 mg, 0.261 mmol, intermediate 60) in DMF (3 mL) was added 1-(bromomethyl)-4-chlorobenzene (70 mg, 0.345 mmol), followed by potassium carbonate (107 mg, 0.775 mmol) and TBAI (5 mg, 0.014 mmol). The mixture was stirred at 60° C. overnight. The reaction was cooled and partitioned between ethyl acetate and water. The combined organic phase was washed with brine, dried over sodium sulfate, and concentrated to give the crude product 7-(4-chlorobenzyl)-1-(4-methoxybenzyl)-3-methyl-8-(3-(3-(trifluoromethoxy)phenoxy)propyl)-1H-purine-2,6(3H,7H)-dione (150 mg, 92.5% yield) as a yellow oil. LCMS retention time 2.075 min; LCMS MH+ 629.

후처리

  1. temperatureThe reaction was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-af9107b33c6d4e50ba54065589cffa6d
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359359B2

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