Hydrochloric Acid → 3-Pentyl-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one

HRID 1664510Notes

Reaction equation

HRID 1664510 reaction equation
C(N[C:10]([N:12]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([NH2:20])=[O:19])=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+].Cl>O>[CH2:21]([N:12]1[C:13]2[N:14]=[CH:15][NH:16][C:17]=2[C:18](=[O:19])[NH:20][C:10]1=[S:11])[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 576001664-[[(Benzoylamino)carbonothioyl](pentyl)amino]-1H-imidazole-5-carboxamide

Product 1

HCID 576002363-Pentyl-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-oneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[[(benzoylamino)carbonothioyl](pentyl)amino]-1H-imidazole-5-carboxamide (11.8 g, 0.0263 mol) and 1 M of sodium hydroxide in water (75 mL) was heated to reflux for 3 h. Solid was formed in the reaction mixture. The reaction mixture was adjusted to pH 3-4 with concentrated HCl with cooling in an ice bath. The solid was filtered, washed with water and air-dried to give the product (9.0 g, 65% purity, 94% yield). The product was used for the next step without further purification. LCMS calculated for C10H15N4OS (M+H): 239.1. found: 239.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customSolid was formed in the reaction mixture
  4. temperaturewith cooling in an ice bath
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customair-dried
  8. customto give the product (9.0 g, 65% purity, 94% yield)
  9. customThe product was used for the next step without further purification

Sources & evidence

ORD record
ord-f1a1213ae8f244a8823d3164d011cc75
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

Loading…