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

HRID 1470270Notes

Reaction equation

HRID 1470270 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-d3f9d92f935d48bb990dbdd5a613dcb5
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

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