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

HRID 2374312Notes

Reaction equation

HRID 2374312 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 (IL) 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 (IL)
  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-ee90d8c7371548ebb6744a965551c873
Source dataset
uspto-grants-2008_12
Patent number
US07462624B2

Reaction notes

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