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Ammonium Hydroxide → 1,1,1,3,3,3-Hexafluoro-2-((9-isopropyl-6-(pyridine-3-ylmethylamino)-9H-purin-2-ylamino)methyl)propan-2-ol

HRID 2047680
ノート
印刷プレビュー

反応式

HRID 2047680 の反応式
F[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.[NH2:31][CH2:32][C:33]([OH:42])([C:38]([F:41])([F:40])[F:39])[C:34]([F:37])([F:36])[F:35].[OH-].[NH4+].FC(F)(F)C1(C(F)(F)F)CO1>CCCCO.CS(C)=O>[F:35][C:34]([F:36])([F:37])[C:33]([CH2:32][NH:31][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1)([OH:42])[C:38]([F:39])([F:41])[F:40]
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 5

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 114694192,2-Bis(trifluoromethyl)oxiraneHCID 115220602-fluoro-9-isopropyl-N-(pyridin-3-ylmethyl)-9H-purin-6-amineHCID 120236773-Amino-1,1,1-trifluoro-2-(trifluoromethyl)propan-2-ol2 回

生成物 1

HCID 25020538
1,1,1,3,3,3-Hexafluoro-2-((9-isopropyl-6-(pyridine-3-ylmethylamino)-9H-purin-2-ylamino)methyl)propan-2-ol
収率 23%

試薬・触媒・溶媒 1

HCID 20476217n-BuOH DMSO溶媒

実験手順

To a stirred solution of 2-fluoro-9-isopropyl-6-[(pyridine-3-ylmethyl)-amino]purine (50 mg, 0,175 mmol) in n-BuOH/DMSO (2.5 ml, 4:1) at room temperature and under an argon atmosphere was added diisopropylethylamine (135 mg, 1.05 mmol) followed by 2-(aminomethyl)-1,1,1,3,3,3-hexafluoropropane-2-ol (prepared from the reaction of 30% ammonium hydroxide with 2,2-bis[trifluoromethyl]oxirane). The reaction mixture was placed in a preheated oil bath at 140° C. and stirred at this temperature for 3 days. The reaction was followed by LCMS and was gone by only 30%. Additional newly prepared 2-(aminomethyl)-1,1,1,3,3,3-hexafluoropropane-2-ol was added and the reaction continued. This addition was done on three more consecutive days to achieve complete conversion. After removal of solvent, the residue was purified by silica gel flash column chromatography to give the title compound as a pale brown powder (19 mg, 23%); δH (CDCl3, 500 MHz) 1.57 (6 H, d, J 7.5, CH[CH3]2), 3.48-3.44 (1 H, m, NHCHHCOH[CF3]2, 3.86-3.81 (1 H, m, NHCHHCOH[CF3]2, 4.62-4.555 (1 H, m, CHMe2), 4.78-4.74 (2 H, m, NHCH2ArH), 5.35 (1H, s, br, OH), 6.36 (1 H, s, br, NH), 7.27-7.22 (2 H, m, ArH), 7.7-7.67 (1 H, m, ArH), 8.5 (1 H, d, J 5, ArH), 8.66 (1 H, s, ArH); δC (CDCl3, 500 MHz) 159.99 (C), 154.63 (C), 149.53 (C), 149.05 (C), 148.6 (CH), 137.79 (C), 135.41 (C), 135.38 (CH), 135 (CH), 123.44 (CH), 75.03 (C), 47.62 (CH2), 46.84 (CH), 42.05 (CH2), 22.1 (2×CH3); m/z 464.2 (M+H)

後処理

  1. customThe reaction mixture was placed in a preheated oil bath at 140° C.
  2. additionThis addition
  3. customAfter removal of solvent
  4. customthe residue was purified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-a6d37526899c4ac7adb33f31a8b2ea05
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592581B2

反応ノート

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