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(4-Bromophenyl)boronic acid → 9-(3-(isopropylamino)propyl)-8-(6-(4-methoxyphenyl)benzo[d][1,3]dioxol-5-ylthio)-9H-purin-6-amine

HRID 521586
ノート
印刷プレビュー

反応式

HRID 521586 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([S:17][C:18]3[N:19]([CH2:28][CH2:29][CH2:30][NH:31][CH:32]([CH3:34])[CH3:33])[C:20]4[C:25]([N:26]=3)=[C:24]([NH2:27])[N:23]=[CH:22][N:21]=4)=[CH:10][C:11]3[O:15][CH2:14][O:13][C:12]=3[CH:16]=2)=[CH:4][CH:3]=1.BrC1C=CC(B(O)O)=CC=1.CC(NCCCN1C(SC2C=[C:67]3[O:69]COC3=CC=2I)=NC2C(N)=NC=NC1=2)C.C([O-])(O)=O.[Na+]>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.CN(C=O)C>[CH:32]([NH:31][CH2:30][CH2:29][CH2:28][N:19]1[C:18]([S:17][C:9]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([O:69][CH3:67])=[CH:3][CH:4]=3)=[CH:16][C:12]3[O:13][CH2:14][O:15][C:11]=3[CH:10]=2)=[N:26][C:25]2[C:20]1=[N:21][CH:22]=[N:23][C:24]=2[NH2:27])([CH3:34])[CH3:33]
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

8

反応物 4

HCID 79599(4-Bromophenyl)boronic acidHCID 516892Sodium BicarbonateHCID 9549213ZelavespibHCID 671167858-(6-(4-bromophenyl)benzo[d][1,3]dioxol-5-ylthio)-9-(3-(isopropylamino)propyl)-9H-purin-6-amine

生成物 1

HCID 671155379-(3-(isopropylamino)propyl)-8-(6-(4-methoxyphenyl)benzo[d][1,3]dioxol-5-ylthio)-9H-purin-6-amine

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

8-(6-(4-bromophenyl)benzo[d][1,3]dioxol-5-ylthio)-9-(3-(isopropylamino)propyl)-9H-purin-6-amine [DZ3-6]. 4-Bromophenylboronic acid (17.6 mg, 0.0877 mmol) was added to PU-H71 (30 mg, 0.0585 mmol) and NaHCO3 (14.7 mg, 0.1755 mmol). DMF (1 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 4 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 13.9 mg (44%) of DZ3-6. 1H NMR (500 MHz, CDCl3) δ 8.23 (s, 1H), 7.44 (d, J=8.2 Hz, 2H), 7.13 (d, J=8.2 Hz, 2H), 7.01 (s, 1H), 6.81 (s, 1H), 6.05 (s, 2H), 5.69 (br s, 2H), 4.08 (t, J=6.0 Hz, 2H), 2.91 (m, 1H), 2.50 (t, J=5.9 Hz, 2H), 1.98 (m, 2H), 1.20 (d, J=6.4 Hz, 6H); 13C NMR (125 MHz, CDCl3/MeOH-d4) δ 154.2, 152.0, 151.2, 149.8, 149.1, 148.2, 139.8, 139.1, 131.2, 131.0, 122.0, 119.0, 117.9, 115.0, 111.1, 102.4, 50.1, 42.1, 40.2, 27.3, 20.2; HRMS (ESI) m/z [M+H]+ calcd. for C24H26BrN6O2S, 541.1021/543.1001; found. 541.1016/543.1004; HPLC: method A Rt=6.93, method B Rt=8.30.

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)
  6. customto give 13.9 mg (44%) of DZ3-6

出典と根拠

ORDレコード
ord-64a77280bf5548e9826ec8be33f0a565
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

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