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Water → 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methyl-7,9-dihydro-8H-purin-8-one

HRID 510123
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HRID 510123 반응식
C(O)=O.[NH2:4][C:5]1[C:10]([NH:11][C:12](=O)[O:13]C)=[C:9]([CH3:16])[N:8]=[C:7]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[N:18]=2)[N:6]=1.O>O1CCCC1>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][N:19]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:25]2[C:17]([C:7]2[N:6]=[C:5]3[C:10]([NH:11][C:12](=[O:13])[NH:4]3)=[C:9]([CH3:16])[N:8]=2)=[N:18]1
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참가 물질

4

반응물 2

HCID 962WaterHCID 86720046Methyl {4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methylpyrimidin-5-yl}carbamate formate

생성물 1

HCID 666142882-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methyl-7,9-dihydro-8H-purin-8-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Under an argon atmosphere, 245 mg (0.60 mmol) of the compound from example 69A were initially charged in tetrahydrofuran (2.6 ml) and cooled to 0° C., and 0.90 ml (0.90 mmol) of bis(trimethylsilyl)sodium amide (1.0 M in tetrahydrofuran) was added dropwise. The mixture was stirred at 0° C. for 1 h and then at RT overnight. Subsequently, the mixture was stirred at 60° C. for 8 h. Thereafter, water was added and the reaction mixture was concentrated. The residue was extracted twice with ethyl acetate, and the collected organic phases were washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. This gave 110 mg (85% purity, 41% of theory) of the title compound in solid form. A solid likewise precipitated out of the aqueous phase, which was filtered off, washed with water and dried under high vacuum. This gave a further 100 mg (44% of theory) of the title compound.

후처리

  1. customat RT
  2. customovernight
  3. stirringSubsequently, the mixture was stirred at 60° C. for 8 h
  4. concentrationthe reaction mixture was concentrated
  5. extractionThe residue was extracted twice with ethyl acetate
  6. washthe collected organic phases were washed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customA solid likewise precipitated out of the aqueous phase, which
  11. filtrationwas filtered off
  12. washwashed with water
  13. customdried under high vacuum

출처 및 근거

ORD 기록
ord-5208600f810347839061c45968f0be15
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096592B2

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