Acetic Acid → 2-(2-amino-5-chlorophenylamino)-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one

HRID 2074160ノート

反応式

HRID 2074160 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:31]([O-])=O)=[C:6]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([NH:13][C:14](=[O:24])[N:15]3[CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:11]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[N:10]=2)[CH:7]=1.C(O)(=O)C.O.[OH-].[NH4+]>[Fe].C(O)C>[NH2:31][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[NH:8][C:9]1[N:17]=[C:16]2[C:12]([NH:13][C:14](=[O:24])[N:15]2[CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:11]([C:25]2[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=2)[N:10]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 576127192-(5-chloro-2-nitrophenylamino)-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one

生成物 1

HCID 670595852-(2-amino-5-chlorophenylamino)-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a vial containing 2-(5-chloro-2-nitrophenylamino)-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one (7 mg, 0.015 mmol) was added glacial acetic acid (0.5 mL), water (1.25 mL) and ethanol (2.5 mL), followed by iron powder (8.4 mg, 0.15 mmol, 10 equiv.) and the resulting mixture heated at 90° C. for 15 min (HPLC monitoring). The reaction mixture was left to cool down to room temperature, concentrated ammonium hydroxide solution was added to bring the pH to basic, and the mixture was stirred for 10 min. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with brine, dried (anhydrous Na2SO4), and the solvent removed in vacuo to give the desired product as a pale yellow solid (yield quantitative). This material was used in the next step without further purification. MS (EI) m/z 438.3 (MH)+.

後処理

  1. waitThe reaction mixture was left
  2. temperatureto cool down to room temperature
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (anhydrous Na2SO4)
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-d7bd77be4fb446e99c3030af657a61c0
出典データセット
uspto-grants-2011_04
特許番号
US07919490B2

反応ノート

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