Benzoyl isothiocyanate → 1-[(4,5-Dimethyl-1H-benzimidazol-2-yl)methyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

HRID 536109Notes

Reaction equation

HRID 536109 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][NH:12][C:13]3[CH:17]=[CH:16][NH:15][C:14]=3[C:18]([O:20]CC)=O)[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:23].C([N:32]=[C:33]=[S:34])(=O)C1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][N:12]3[C:13]4[CH:17]=[CH:16][NH:15][C:14]=4[C:18](=[O:20])[NH:32][C:33]3=[S:34])[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:23]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 67068491Ethyl 3-{[(4,5-dimethyl-1H-benzimidazol-2-yl)methyl]amino}-1H-pyrrole-2-carboxylate

Product 1

HCID 115733931-[(4,5-Dimethyl-1H-benzimidazol-2-yl)methyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-oneYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-{[(4,5-dimethyl-1H-benzimidazol-2-yl)methyl]amino}-1H-pyrrole-2-carboxylate (0.043 g, 0.14 mmol) was dissolved in CH2Cl2 (1.5 mL) and benzoyl isothiocyanate (0.026 g, 0.16 mmol) was added. After stirring at r.t. for 1 h the solvent was removed in vacuo. The residue was dissolved in ammonia (7N in methanol) and heated to 70° C. for 2 h in a sealed vessel. The solvent was removed in vacuo and the residue was purified by preparative HPLC, obtaining a white solid, 0.008 g (18%) of the title compound, as a tautomeric mixture (1:1).

Workup

  1. customwas removed in vacuo
  2. dissolutionThe residue was dissolved in ammonia (7N in methanol)
  3. temperatureheated to 70° C. for 2 h in a sealed vessel
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6cda8ec78ab547c780e8d0c7297f8636
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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