Potassium Carbonate → 8-(cyclopentyloxy)-3-methyl-7-((4-methylthiazol-2-yl)methyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200680노트

반응식

HRID 2200680 반응식
[CH:1]1([O:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH2:19][O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:11](=[O:27])[N:10]([CH3:28])[C:9]=3[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:30][C:31]1[S:32][CH:33]=[C:34]([CH3:36])[N:35]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH:1]1([O:6][C:7]2[N:15]([CH2:30][C:31]3[S:32][CH:33]=[C:34]([CH3:36])[N:35]=3)[C:14]3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH2:19][O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:11](=[O:27])[N:10]([CH3:28])[C:9]=3[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 112750912-(Chloromethyl)-4-methyl-1,3-thiazole2회HCID 904028818-(cyclopentyloxy)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione

생성물 1

HCID 904029518-(cyclopentyloxy)-3-methyl-7-((4-methylthiazol-2-yl)methyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a solution of 8-(cyclopentyloxy)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (0.12 g, 0.31 mmol) in DMF (5 mL) was added 2-(chloromethyl)-4-methylthiazole (91 mg, 0.62 mmol, intermediate 54), potassium carbonate (85 mg, 0.62 mmol), and TBAI (2 mg, 0.02 mmol). The reaction was heated at 50° C. overnight. The mixture was cooled and partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product which was used without purification. LCMS retention time 1.704 min; LCMS MH+-THP 470.

후처리

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a119737ef4d248ff98d667da65813883
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359359B2

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