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

HRID 249773

Reaction equation

HRID 249773 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-99449ac337b44cea915d1044d61e9d8f
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Linked notes

Loading…