Triethylamine → 1-(1H-Imidazol-5-ylmethyl)-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

HRID 536102Notes

Reaction equation

HRID 536102 reaction equation
Cl.C(O[C:5]([C:7]1[NH:8][CH:9]=[CH:10][C:11]=1[NH2:12])=[O:6])C.[CH:13]([C:15]1[N:16]=[CH:17][NH:18][CH:19]=1)=O.[BH3-]C#N.[Na+].CCN(CC)CC.C([N:39]=[C:40]=[S:41])(=O)C1C=CC=CC=1>CO>[NH:16]1[C:15]([CH2:13][N:12]2[C:11]3[CH:10]=[CH:9][NH:8][C:7]=3[C:5](=[O:6])[NH:39][C:40]2=[S:41])=[CH:19][N:18]=[CH:17]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 68284Benzoyl isothiocyanateHCID 764281H-Imidazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 164270913-Amino-2-ethoxycarbonylpyrrole hydrochloride

Product 1

HCID 116732051-(1H-Imidazol-5-ylmethyl)-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-oneYield 13.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-1H-pyrrole-2-carboxylic acid ethyl ester hydrochloride (0.10 g, 0.52 mmol) was dissolved in methanol (4 mL) and 4-formylimidazole (0.060 g, 0.63 mmol), NaCNBH3 (0.033 g, 0.52 mmol) and Et3N (0.073 g, 0.52 mmol) were added. The resulting mixture was stirred at r.t. overnight. The solvent was removed in vacuo and the residue was dissolved in CH2Cl2 (3 mL) and methanol (1 mL). Benzoyl isothiocyanate (0.078 mL, 0.58 mmol) was added and after stirring at r.t. for 30 minutes the mixture was concentrated in vacuo. The residue was dissolved in ammonia (7N in methanol, 3 mL) and heated at 80° C. for 1 h. The precipitated product was filtered and washed with methanol, followed by diethyl ether. The crude product was purified by preparative HPLC, obtaining 0.017 g (13%) of the title compound as a solid. OC 710/07

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (3 mL)
  3. stirringafter stirring at r.t. for 30 minutes the mixture
  4. concentrationwas concentrated in vacuo
  5. dissolutionThe residue was dissolved in ammonia (7N in methanol, 3 mL)
  6. temperatureheated at 80° C. for 1 h
  7. filtrationThe precipitated product was filtered
  8. washwashed with methanol
  9. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-8df471470c194193998dd4ad29a66638
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

Loading…