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

HRID 249773노트

반응식

HRID 249773 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-99449ac337b44cea915d1044d61e9d8f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863285B2

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