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

HRID 2234933ノート

反応式

HRID 2234933 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-9951eaa6c45c4514bba5e0262cb62958
出典データセット
uspto-grants-2010_05
特許番号
US07713982B2

反応ノート

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