Potassium Carbonate → HCID 90402626、化合物

HRID 2200707ノート

反応式

HRID 2200707 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 132043233-Hydroxybutyl 4-methylbenzenesulfonateHCID 90402690HCID 90402690、化合物2 回

生成物 1

HCID 90402626HCID 90402626、化合物収率 26%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ab2429b57f44f769d9412966fb6c234
出典データセット
uspto-grants-2016_06
特許番号
US09359359B2

反応ノート

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