Ethyl isothiocyanatoformate → 3-[(6-Phenoxypyridin-3-yl)methyl]-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one

HRID 912718Notes

Reaction equation

HRID 912718 reaction equation
C(OC(N=[C:7]=[S:8])=O)C.[O:9]([C:16]1[N:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]2[N:25]=[CH:26][NH:27][C:28]=2[C:29]([NH2:31])=[O:30])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCl>[O:9]([C:16]1[N:21]=[CH:20][C:19]([CH2:22][N:23]2[C:24]3[N:25]=[CH:26][NH:27][C:28]=3[C:29](=[O:30])[NH:31][C:7]2=[S:8])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 674149314-{[(6-Phenoxypyridin-3-yl)methyl]amino}-1H-imidazole-5-carboxamide

Product 1

HCID 248556313-[(6-Phenoxypyridin-3-yl)methyl]-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-oneYield 12.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethoxycarbonyl isothiocyanate (0.096 mL, 0.85 mmol) was added to 4-{[(6-phenoxypyridin-3-yl)methyl]amino}-1H-imidazole-5-carboxamide (0.25 g, 0.81 mmol, obtained from Example 25(a)) in anhydrous dichloromethane (3.0 mL). After stirring for 2.5 h at ambient temperature the mixture was concentrated to dryness. Sodium hydroxide (10 mL, 2% w/v) was added and the solution was heated at 50° C. over night. After cooling, the pH was adjusted to 4-5 using 2N HCl. The solid was collected by filtration and recrystallized from DMSO/water to give a white crystalline material. A portion of this material was recrystallized from MeOH to give 35 mg (0.10 mmol, 12% yield) of the title compound.

Workup

  1. concentrationwas concentrated to dryness
  2. additionSodium hydroxide (10 mL, 2% w/v) was added
  3. temperaturethe solution was heated at 50° C. over night
  4. temperatureAfter cooling
  5. filtrationThe solid was collected by filtration
  6. customrecrystallized from DMSO/water
  7. customto give a white crystalline material
  8. customA portion of this material was recrystallized from MeOH

Sources & evidence

ORD record
ord-2591b12836e44902b78838ed8eebe95f
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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