Potassium Carbonate → HCID 90402626, 화합물

HRID 2200707노트

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HRID 2200707 반응식
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=3)[C:6]=2[C:5](=[O:31])[NH:4][C:3]1=[O:32].[OH:33][CH:34]([CH3:48])[CH2:35][CH2:36]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:33][CH:34]([CH3:48])[CH2:35][CH2:36][N:4]1[C:5](=[O:31])[C:6]2[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=3)[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:32]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 132043233-Hydroxybutyl 4-methylbenzenesulfonateHCID 90402690HCID 90402690, 화합물2회

생성물 1

HCID 90402626HCID 90402626, 화합물수율 26%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

To a solution of 3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (30 mg, 0.067 mmol, intermediate 51) in DMF (3 mL) was added 3-hydroxybutyl-4-methylbenzenesulfonate (24.68 mg, 0.10 mmol), followed by potassium carbonate (27.93 mg, 0.20 mmol). The reaction was stirred at 70° C. for 4 h. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product, which was purified by preparative HPLC to give 1-(3-hydroxybutyl)-3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (9 mg, 25.8%) as white solid. 1H-NMR (CD3OD) δ 8.216(s,1H), 7.491-7.467(d,1H), 7.312-7.272(m,1H), 7.154-6.995(m,4H), 5.688(s,2H), 4.305(s,2H), 4.143-4.011(m,2H), 3.772-3.440(m,1H), 3.585(s, 3H), 2.283(s,3H), 1.761-1.703(m,2H), 1.194-1.179(d,3H). LCMS retention time 2.569 min; LCMS MH+ 518.

후처리

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-4ab2429b57f44f769d9412966fb6c234
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359359B2

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