1,1'-Carbonyldiimidazole → 7H-Purin-8-ol

HRID 2406891Notes

Reaction equation

HRID 2406891 reaction equation
[N:1]1[CH:6]=[C:5]([NH2:7])[C:4]([NH2:8])=[N:3][CH:2]=1.[C:9](N1C=CN=C1)(N1C=CN=C1)=[O:10]>O1CCOCC1>[N:1]1[CH:6]=[C:5]2[C:4]([NH:8][C:9](=[O:10])[NH:7]2)=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 837034,5-Diaminopyrimidine

Product 1

HCID 2297717H-Purin-8-olYield 567.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Pyrimidine-4,5-diamine (1.1 g, 10 mmol) and 1,1′-carbonyl diimidazole 1.78 g, 1.1 mmol) were added to dioxane (15 mL) and the reaction mixture was stirred at 90° C. for 48 hours. The mixture was cooled and the precipitate was recovered by filtration, rinsed with cold dioxane, and dried to give 850 mg (61%) of 7,9-dihydro-purin-8-one.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate was recovered by filtration
  3. washrinsed with cold dioxane
  4. customdried

Sources & evidence

ORD record
ord-0ba2525ed6324bc6b28225dea4d0f0b5
Source dataset
uspto-grants-2014_08
Patent number
US08809402B2

Reaction notes

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