Hydrochloric Acid → 1-[(6-Oxo-1,6-dihydropyridin-2-yl)methyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

HRID 536095Notes

Reaction equation

HRID 536095 reaction equation
C([N:9]=[C:10]=[S:11])(=O)C1C=CC=CC=1.C(O[C:15]([C:17]1[NH:18][CH:19]=[CH:20][C:21]=1[NH:22][CH2:23][C:24]1[NH:25][C:26](=[O:30])[CH:27]=[CH:28][CH:29]=1)=[O:16])C.C(=O)([O-])[O-].[K+].[K+].Cl>C(Cl)Cl>[O:30]=[C:26]1[NH:25][C:24]([CH2:23][N:22]2[C:21]3[CH:20]=[CH:19][NH:18][C:17]=3[C:15](=[O:16])[NH:9][C:10]2=[S:11])=[CH:29][CH:28]=[CH:27]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 67068502HCID 67068502, compound

Product 1

HCID 116947331-[(6-Oxo-1,6-dihydropyridin-2-yl)methyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzoyl isothiocyanate (0.27 g, 1.6 mmol) dissolved in CH2Cl2 (3 mL) was added to 3-{[(6-oxo-1,6-dihydropyridin-2-yl)methyl]amino}-1H-pyrrole-2-carboxylic acid ethyl ester (0.25 g, 0.96 mmol) in CH2Cl2 (7 mL). The resulting mixture was stirred at r.t. overnight. The solvent was removed in vacuo and the residue was dissolved in methanol (15 mL) and potassium carbonate (0.50 g, 3.6 mmol) was added. The reaction mixture was stirred at 50° C. for 6.5 h. After cooling to r.t., 1M HCl was added dropwise until a neutral pH was obtained.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methanol (15 mL)
  3. stirringThe reaction mixture was stirred at 50° C. for 6.5 h
  4. temperatureAfter cooling to r.t.
  5. customwas obtained

Sources & evidence

ORD record
ord-c8f8a65874614a1cb5b5ce78900447c7
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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