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

HRID 510141
ノート
印刷プレビュー

反応式

HRID 510141 の反応式
COC1C=C(OC)C=CC=1C[N:6]1[C:14](=[O:15])[N:13]([CH2:16][CH:17]2[CH2:20][CH2:19][O:18]2)[C:12]2[C:7]1=[N:8][C:9]([C:21]1[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])[N:22]=1)=[N:10][CH:11]=2.C([SiH](CC)CC)C.O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[F:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][N:23]1[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:29]2[C:21]([C:9]2[N:8]=[C:7]3[C:12]([N:13]([CH2:16][CH:17]4[CH2:20][CH2:19][O:18]4)[C:14](=[O:15])[NH:6]3)=[CH:11][N:10]=2)=[N:22]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 666140889-(2,4-Dimethoxybenzyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-(oxetan-2-ylmethyl)-7,9-dihydro-8H-purin-8-one

生成物 1

HCID 666135192-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-(oxetan-2-ylmethyl)-7,9-dihydro-8H-purin-8-one収率 48.9%

試薬・触媒・溶媒 2

HCID 6422Trifluoroacetic acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

476 mg (0.82 mmol) of the compound from example 86A were dissolved in 15 ml of trifluoroacetic acid, 953 mg (8.20 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). 173 mg of the title compound were obtained (49% of theory).

後処理

  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)

出典と根拠

ORDレコード
ord-24fa3137c4c1484f8f0c0646a0926f87
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096592B2

反応ノート

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