Hydroxyamine hydrochloride → 3-butyl-1-methyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile

HRID 1943802ノート

反応式

HRID 1943802 の反応式
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([CH:14]=O)[N:10]([CH2:16][CH:17]=[CH2:18])[C:9]=2[C:8](=[O:19])[N:7]([CH3:20])[C:6]1=[O:21])[CH2:2][CH2:3][CH3:4].Cl.[NH2:23]O>N1C=CC=CC=1>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([C:14]#[N:23])[N:10]([CH2:16][CH:17]=[CH2:18])[C:9]=2[C:8](=[O:19])[N:7]([CH3:20])[C:6]1=[O:21])[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 592995903-butyl-1-methyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbaldehyde

生成物 1

HCID 592995553-butyl-1-methyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
50 °C

実験手順

A solution of 3-butyl-1-methyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbaldehyde in anhydrous pyridine (5 ml) was treated with hydroxylamine hydrochloride (63 mg, 0.91 mmol) and heated at 50° C. for 1 hour. The mixture was allowed to cool, concentrated, and treated with acetic anhydride (5 ml) then heated at 100° C. for 2.5 hours and 125° C. for 45 minutes. Again the mixture was allowed to cool then partitioned between water and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated to afford the title compound as a yellow residue (230 mg crude, 114%); m/z 288.3[MH+].

後処理

  1. temperatureto cool
  2. concentrationconcentrated
  3. additiontreated with acetic anhydride (5 ml)
  4. temperaturethen heated at 100° C. for 2.5 hours and 125° C. for 45 minutes
  5. temperatureto cool
  6. customthen partitioned between water and EtOAc
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-fe109db5dcfd4f0a8f154682440a3ef8
出典データセット
uspto-grants-2013_03
特許番号
US08394808B2

反応ノート

読み込み中…