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Dimethylformamide → 8-(6-(4-tert-butylphenyl)benzo[d][1,3]-dioxol-5-ylthio)-9-(3-(isopropylamino)propyl)-9H-purin-6-amine

HRID 521581
ノート
印刷プレビュー

反応式

HRID 521581 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][CH:15]([NH:17][CH2:18][CH2:19][CH2:20][N:21]1[C:30]([S:31][C:32]2[CH:37]=[C:36]3[O:38][CH2:39][O:40][C:35]3=[CH:34][C:33]=2I)=[N:29][C:23]2[C:24]([NH2:28])=[N:25][CH:26]=[N:27][C:22]1=2)[CH3:16].C([O-])(O)=O.[Na+].CN(C=O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:33]2[C:32]([S:31][C:30]3[N:21]([CH2:20][CH2:19][CH2:18][NH:17][CH:15]([CH3:16])[CH3:14])[C:22]4[C:23]([N:29]=3)=[C:24]([NH2:28])[N:25]=[CH:26][N:27]=4)=[CH:37][C:36]3[O:38][CH2:39][O:40][C:35]=3[CH:34]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
参加物反応条件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 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 9549213Zelavespib

生成物 1

HCID 671159988-(6-(4-tert-butylphenyl)benzo[d][1,3]-dioxol-5-ylthio)-9-(3-(isopropylamino)propyl)-9H-purin-6-amine収率 83%

試薬・触媒・溶媒 2

HCID 178418476
HCID 178418476、化合物
触媒
HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

4-tert-Butylphenylboronic acid (15.6 mg, 0.0876 mmol) was added to PU-H71 (30 mg, 0.0585 mmol) and NaHCO3 (14.7 mg, 0.1755 mmol). DMF (0.5 mL) was added and the reaction mixture was evacuated and back filled with nitrogen. This was repeated four times then nitrogen was bubbled through the reaction mixture for 10 minutes. Then H2O (0.1 mL) and Pd(PPh3)2Cl2 (4 mg, 0.00584 mmol) were added and the reaction mixture was heated under nitrogen at 90° C. for 3 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (hexane:CH2Cl2:EtOAc:MeOH—NH3 (7N), 4:5:2:1) to give 25.0 mg (83%) of DZ2-390. 1H NMR (500 MHz, MeOH-d4) δ 8.11 (s, 1H), 7.27 (d, J=8.4 Hz, 2H), 7.14 (s, 1H), 7.12 (d, J=8.4 Hz, 2H), 6.86 (s, 1H), 6.06 (s, 2H), 3.93 (t, J=6.9 Hz, 2H), 2.92 (septet, J=6.5 Hz, 1H), 2.61 (t, J=7.3 Hz, 2H), 1.86 (m, 2H), 1.28 (s, 9H), 1.12 (d, J=6.5 Hz, 6H); 13C NMR (125 MHz, MeOH-d4) δ 155.9, 153.3, 151.9, 151.8, 150.9, 150.2, 149.2, 141.9, 138.8, 130.0, 125.9, 120.4, 120.3, 115.4, 112.3, 103.6, 50.6, 44.0, 41.8, 35.4, 31.8, 29.3, 21.1; HRMS (ESI) m/z [M+H]+ calcd. for C28H35N6O2S, 519.2542; found. 519.2545; HPLC: method A Rt=7.43, method B Rt=9.45.

後処理

  1. customthe reaction mixture was evacuated
  2. additionback filled with nitrogen
  3. customnitrogen was bubbled through the reaction mixture for 10 minutes
  4. customSolvent was removed under reduced pressure
  5. customthe resulting residue was purified by preparatory TLC (hexane:CH2Cl2:EtOAc:MeOH—NH3 (7N), 4:5:2:1)

出典と根拠

ORDレコード
ord-cf6025c3ba524287934d6f3c7c9946ec
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09328114B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート