1,1'-Carbonyldiimidazole → 6-CHLORO-7H-PURIN-8(9H)-ONE

HRID 1685182Notes

Reaction equation

HRID 1685182 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11]>O1CCOCC1>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[NH:9][C:10](=[O:11])[NH:8]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 780104,5-Pyrimidinediamine, 6-chloro-

Product 1

HCID 576592036-CHLORO-7H-PURIN-8(9H)-ONEYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Combine 6-chloro-pyrimidine-4,5-diamine (7.46 mmol; 1.08 g); 1,1′-carbonyldiimidazole (2 equiv; 14.92 mmol; 2.42 g) and 1,4-dioxane (20 mL) and heat to reflux under nitrogen for 50 min. Evaporate the yellow solution to an oil. Add DCM (80 mL), let sit 1 h, filter and dry in vacuum oven at 45° C. to provide the title compound (1.22 g; 7.15 mmol; 96%) MS (ES+): m/z=169 (M−H).

Workup

  1. temperatureto reflux under nitrogen for 50 min
  2. customEvaporate the yellow solution to an oil
  3. filtrationfilter
  4. customdry in vacuum oven at 45° C.

Sources & evidence

ORD record
ord-4db3e9c1192c4811b3af7f7b6328f77f
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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