1,4-Dioxane → 6-Chloro-7-ethyl-7,9-dihydro-8H-purin-8-one

HRID 2405988Notes

Reaction equation

HRID 2405988 reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([NH2:11])=[N:6][CH:7]=[N:8][C:9]=1[Cl:10])[CH3:2].[O:12]1CCOC[CH2:13]1>>[CH2:1]([N:3]1[C:4]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[Cl:10])[NH:11][C:13]1=[O:12])[CH3:2]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 578991686-Chloro-N5-ethyl-4,5-pyrimidinediamine

Product 1

HCID 578991466-Chloro-7-ethyl-7,9-dihydro-8H-purin-8-oneYield 60%

Procedure

A solution of N5-ethyl-6-chloropyrimidine-4,5-diamine (0.21 g, 1.22 mmol) and 1,1-carbonyldiimidazole (0.40 g, 2.44 mmol) in 1,4-dioxane (5 mL) was degassed, flushed with nitrogen and refluxed under nitrogen for 22 h. The solution was cooled and partitioned between ethyl acetate (15 mL), 1M hydrochloric acid (10 mL) and brine (5 mL). The organic layer was dried, filtered and concentrated to give 7-ethyl-6-chloro-7,9-dihydropurin-8-one (0.146 g, 0.735 mmol, 60%) as a yellow solid. LC-MS (LCT2) m/z 199, 201 [M+H+], Rt 4.62 min.

Workup

  1. customflushed with nitrogen
  2. temperaturerefluxed under nitrogen for 22 h
  3. temperatureThe solution was cooled
  4. custompartitioned between ethyl acetate (15 mL), 1M hydrochloric acid (10 mL) and brine (5 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6f0a404eae024dcb80e31e25f4115c53
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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