Pentanal → 4-(pentylamino)-1H-imidazole-5-carbonitrile

HRID 600583

反応式

HRID 600583 の反応式
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]#[N:8].[CH:9](=O)[CH2:10][CH2:11][CH2:12][CH3:13].C([BH3-])#N.[Na+]>CO>[CH2:9]([NH:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]#[N:8])[CH2:10][CH2:11][CH2:12][CH3:13]

参加物

5

反応物 3

HCID 8063PentanalHCID 787775-amino-1H-imidazole-4-carbonitrileHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 451205654-(pentylamino)-1H-imidazole-5-carbonitrile収率 70%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-amino-1H-imidazole-5-carbonitrile (10.0 g, 0.0925 mol) and pentanal (11 mL, 0.10 mol) were mixed in methanol (100 mL). After stirring at room temperature for 2 hours, Sodium cyanoborohydride (7.0 g, 0.11 mol) was added to the mixture. The mixture was continued to stir overnight. The reaction mixture was concentrated, diluted with EtOAc (1 L) and washed with sat. NaHCO3 (30 ml) and then brine (50 ml) solutions respectively. The organic layers were dried over Na2SO4, concentrated and purified with combi-flash silica gel chromatography (20%-80% EtOAc in hexane) to yield the desired product (11.5 g, 70%). LCMS calculated for C9H15N4(M+H): 179. found: 179.1.

後処理

  1. stirringto stir overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with EtOAc (1 L)
  4. washwashed with sat. NaHCO3 (30 ml)
  5. dry with materialThe organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified with combi-flash silica gel chromatography (20%-80% EtOAc in hexane)

出典と根拠

ORDレコード
ord-b0f294ccbc304a73aefd5ea259d0518a
出典データセット
uspto-grants-2011_03
特許番号
US07902205B2

関連ノート

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