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Potassium Carbonate → 7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-8-((5-methylpyridin-3-yl)oxy)-1H-purine-2,6(3H,7H)-dione

HRID 2200720
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HRID 2200720 반응식
Cl[C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH2:22][OH:23])[C:6](=[O:24])[N:5]([CH2:25][CH3:26])[C:4]=2[N:3]=1.[CH3:27][C:28]1[CH:29]=[C:30]([OH:34])[CH:31]=[N:32][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:10]2[C:9]3[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH2:22][OH:23])[C:6](=[O:24])[N:5]([CH2:25][CH3:26])[C:4]=3[N:3]=[C:2]2[O:34][C:30]2[CH:31]=[N:32][CH:33]=[C:28]([CH3:27])[CH:29]=2)=[CH:13][CH:14]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2247533-Hydroxy-5-methylpyridineHCID 904026398-chloro-7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione2회

생성물 1

HCID 904031417-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-8-((5-methylpyridin-3-yl)oxy)-1H-purine-2,6(3H,7H)-dione수율 22.5%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
80 °C

실험 절차

To a solution of 8-chloro-7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (30 mg, 0.08 mmol, intermediate 78) in DMF (2 mL) was added 5-methylpyridin-3-ol (12.36 mg, 0.12 mmol), followed by potassium carbonate (15.66 mg, 0.11 mmol). The reaction was stirred at 80° C. for 3 h. The reaction was cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, and concentrated to give a crude product, which was purified by preparative HPLC to give 7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-8-((5-methylpyridin-3-yl)oxy)-1H-purine-2,6(3H,7H)-dione (8 mg, 22.5%) as white solid. 1H-NMR (CD3OD) δ 8.35-8.42(d, 2H), 7.68(s, 1H), 7.38-7.48(m, 4H), 5.52(s, 2H), 4.01-4.14(m, 4H), 3.61-3.64(m, 2H), 2.43(s, 3H), 1.87-1.90(m, 2H), 1.22-1.26(m, 3H). LCMS retention time 2.511 min; LCMS MH+ 470.

후처리

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

출처 및 근거

ORD 기록
ord-320f9217cd52407485bf8ced66212da1
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359359B2

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