Acetic Acid → 4-amino-3-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-ylamino)benzonitrile

HRID 600439ノート

反応式

HRID 600439 の反応式
[Cl:1][C:2]1[N:10]=[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=2[N+:20]([O-])=O)[C:15]#[N:16])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:23])[NH:6]2.C(O)(=O)C.O.[NH4+].[OH-]>[Fe].C(O)C>[NH2:20][C:19]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[NH:11][C:9]1[N:8]=[C:7]2[C:3]([NH:4][C:5](=[O:23])[NH:6]2)=[C:2]([Cl:1])[N:10]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 576127083-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-ylamino)-4-nitrobenzonitrile

生成物 1

HCID 866229404-amino-3-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-ylamino)benzonitrile

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 3-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-ylamino)-4-nitrobenzonitrile (0.41 g, 1.23 mmol) was added glacial acetic acid (30 mL), water (75 mL) and ethanol (150 mL), followed by iron powder (Aldrich, 0.69 g, 12.3 mmol, 10 equiv.) and the reaction mixture was stirred at 90° C. for 15 min (LC-MS monitoring), when it became a clear dark orange solution. It was cooled to r.t., then concentrated NH4OH (50 mL) was added to bring the pH to 11. The reaction mixture was stirred at r.t. for 30 min. Repeated extractions into ethyl acetate, then into 25% isopropanol in CH2Cl2 (total volume 2 L), drying of the combined organic extracts, and in vacuo evaporation of the solvent provided the desired product as a brown solid, which was used in the next step without further purification. MS (EI) m/z 302.1 (MH)+.

後処理

  1. temperatureIt was cooled to r.t.
  2. stirringThe reaction mixture was stirred at r.t. for 30 min
  3. extractionextractions into ethyl acetate
  4. dry with materialinto 25% isopropanol in CH2Cl2 (total volume 2 L), drying of the combined organic extracts
  5. customin vacuo evaporation of the solvent

出典と根拠

ORDレコード
ord-9cdb1ea987244e87af8ad132f31d7d29
出典データセット
uspto-grants-2011_03
特許番号
US07902187B2

反応ノート

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