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

HRID 600439노트

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HRID 600439 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-9cdb1ea987244e87af8ad132f31d7d29
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902187B2

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