Isopropyl iodide → 6-Chloro-9-isopropyl-9h-purin-2-amine

HRID 1422477ノート

反応式

HRID 1422477 の反応式
[H-].[Na+].[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][NH:10]2)=[C:6]([Cl:13])[N:5]=1.I[CH:15]([CH3:17])[CH3:16]>CN(C=O)C>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH:15]([CH3:17])[CH3:16])=[C:6]([Cl:13])[N:5]=1

参加物

5

反応物 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 1785084356-chloro-1H-purin-2-amine

生成物 1

HCID 219337716-Chloro-9-isopropyl-9h-purin-2-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (1.5 g of 60% dispersion in mineral oil, 38 mmol) was added in portions over 10 min to a stirred suspension of 2-amino-6-chloro-9H-purine (5.34 g, 31.5 mmol) in anhydrous DMF (50 mL) at rt. After 45 min, the mixture was cooled in an ice bath, then 2-iodopropane was added. The cooling bath was removed and the stirred mixture was allowed to warm to rt over 16 h. The mixture was cooled in ice, then water was added. The mixture was concentrated, and the residue was treated with hot ethyl acetate. The cooled mixture was filtered, and the filtrate was concentrated. The residue was purified by column chromatography on silica gel, eluting with 0 to 50% EtOAc in hexane to afford the title compound as a solid. 1H NMR (400 MHz, CDCl3) δ 7.83 (s, 1H), 5.17 (s, 2H), 4.71-4.66 (m, 1H), 1.57 (d, 6H). MS m/z 212.1 (M+1).

後処理

  1. temperaturethe mixture was cooled in an ice bath
  2. customThe cooling bath was removed
  3. temperatureThe mixture was cooled in ice
  4. additionwater was added
  5. concentrationThe mixture was concentrated
  6. additionthe residue was treated with hot ethyl acetate
  7. filtrationThe cooled mixture was filtered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with 0 to 50% EtOAc in hexane

出典と根拠

ORDレコード
ord-c568da62b92444bd930e271703c4eb3a
出典データセット
uspto-grants-2015_01
特許番号
US08927281B2

反応ノート

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