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

HRID 1036334Notes

Reaction equation

HRID 1036334 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-665c847ff62b4762b85c5d3856e05321
Source dataset
uspto-grants-2013_10
Patent number
US08546407B2

Reaction notes

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