Pentanal → HCID 57600193, compound

HRID 2368551Notes

Reaction equation

HRID 2368551 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([NH2:9])=[O:8].[CH:10](=O)[CH2:11][CH2:12][CH2:13][CH3:14].C([BH3-])#N.[Na+]>CO>[CH2:10]([NH:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([NH2:9])=[O:8])[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8063PentanalHCID 96795-Aminoimidazole-4-carboxamideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 57600193HCID 57600193, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Amino-1H-imidazole-5-carboxamide (13.0 g, 0.104 mol) and valeraldehyde (11 mL, 0.10 mol) were mixed in methanol (200 mL). After being stirred for 30 min, sodium cyanoborohydride (6.5 g, 0.10 mol) was added to the solution and stirring was continued overnight. The reaction mixture was concentrated under reduced pressure. The remaining residue was taken up in EtOAc and the resulting solution was washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried (MgSO4) and concentrated. The residue was purified by flash chromatography (DCM to 5% MeOH/DCM) to give the desired product (12.9 g, 63.1%). LCMS calculated for C9H16N4O (M+H): 197.1. Found: 180.1 (M+H−NH3).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe resulting solution was washed with saturated NaHCO3
  5. extractionThe aqueous layer was extracted with EtOAc three times
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (DCM to 5% MeOH/DCM)

Sources & evidence

ORD record
ord-c79e9e58b6664be5a3a9385c123a4d6a
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

Loading…