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

HRID 510139
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HRID 510139 반응식
[CH:1]1([CH2:4][N:5]2[C:13]3[C:8](=[N:9][C:10]([C:14]4[C:22]5[C:17](=[N:18][CH:19]=[CH:20][CH:21]=5)[N:16]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[F:30])[N:15]=4)=[N:11][CH:12]=3)[N:7](CC3C=CC(OC)=CC=3OC)[C:6]2=[O:42])[CH2:3][CH2:2]1.C([SiH](CC)CC)C.O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[CH:1]1([CH2:4][N:5]2[C:13]3[C:8](=[N:9][C:10]([C:14]4[C:22]5[C:17](=[N:18][CH:19]=[CH:20][CH:21]=5)[N:16]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[F:30])[N:15]=4)=[N:11][CH:12]=3)[NH:7][C:6]2=[O:42])[CH2:3][CH2:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 666141447-(Cyclopropylmethyl)-9-(2,4-dimethoxybenzyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,9-dihydro-8H-purin-8-one

생성물 1

HCID 666351437-(Cyclopropylmethyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,9-dihydro-8H-purin-8-one수율 53.6%

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid용매HCID 8857Ethyl Acetate용매

실험 절차

482 mg (0.70 mmol) of the compound from example 84A were dissolved in 21 ml of trifluoroacetic acid, 817 mg (7.02 mmol) of triethylsilane were added and the mixture was heated to reflux for 18 h. The reaction mixture was admixed with water and ethyl acetate, and neutralized with saturated aqueous sodium hydrogencarbonate solution. The organic phase was dried over sodium sulfate and concentrated on a rotary evaporator. The residue was dried under high vacuum, and purified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10). 156 mg of the title compound were obtained (53% of theory).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was dried under high vacuum
  6. custompurified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10)

출처 및 근거

ORD 기록
ord-b225ebb6893542b0a291fb3cb2ae91f9
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096592B2

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