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Acetonitrile → 1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 897456
ノート
印刷プレビュー

反応式

HRID 897456 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]1[C:27]2([CH2:32][CH2:31][CH:30]([N:33]3[C:37]4=[N:38][CH:39]=[N:40][C:41]([NH2:42])=[C:36]4[C:35](I)=[N:34]3)[CH2:29][CH2:28]2)[O:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)C>[O:23]1[C:27]2([CH2:28][CH2:29][CH:30]([N:33]3[C:37]4=[N:38][CH:39]=[N:40][C:41]([NH2:42])=[C:36]4[C:35]([C:11]4[CH:10]=[N:9][C:8]([O:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[CH:13][CH:12]=4)=[N:34]3)[CH2:31][CH2:32]2)[O:26][CH2:25][CH2:24]1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 223467202-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 223470211-(1,4-dioxaspiro[4.5]dec-8-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine2 回

生成物 1

HCID 223471771-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine収率 71.9%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Intermediate AG) (1.1 g, 0.0037 mol), 1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate N) (1.29 g, 0.0032 mol), tetrakis(triphenylphosphine)palladium (0.22 g, 0.00019 mol) and sodium carbonate (0.85 g, 0.008 mol) was heated in a mixture of ethylene glycol dimethyl ether (40 mL) and water (20 mL) at 80° C. for 16 hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and ethylene glycol dimethyl ether was removed under reduced pressure. The precipitate was collected by filtration, washed with water once, acetonitrile twice and diethyl ether twice to give 1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine as an off-white solid (1.03 g, 0.0023 mol): 1H NMR (DMSO-d6, 400 MHz) 8.36 (s, 1H), 8.24 (s, 1H), 8.03 (d, 1H), 7.45 (t, 2H), 7.22 (m, 3H), 7.16 (d, 1H), 4.81 (m, 1H), 3.93 (s, 4H), 2.24 (m, 2H), 1.88 (m, 6H); MS: MH+ 445.

後処理

  1. customethylene glycol dimethyl ether was removed under reduced pressure
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water once

出典と根拠

ORDレコード
ord-af68a0b5d96d4a84a784549cdec8c7d1
出典データセット
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06921763B2

反応ノート

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