Sodium Hydroxide → 2,6-dichloro-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 2100518Notes

Reaction equation

HRID 2100518 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:11]=[C:10]([Cl:12])[CH:9]=[N:8][C:6]=2[N:7]=1.[OH-:14].[Na+]>>[Cl:1][C:2]1[NH:3][C:4](=[O:14])[C:5]2[CH:11]=[C:10]([Cl:12])[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 866166012,4,6-Trichloropyrido[2,3-d]pyrimidine

Product 1

HCID 1363459252,6-dichloro-3H-pyrido[2,3-d]pyrimidin-4-one

Procedure

2,4,6-Trichloro-pyrido[2,3-d]pyrimidine (360 mg, crude) was dissolved in 1N NaOH (6 ml) (ultrasonication) and stirred for 30 min at r.t. The obtained suspension was extracted with Et2O. The water layer was separated, acidified (HCl), and again extracted (EtOAc). The organic layer was dried (Na2SO4), filtered and evaporated to give crude 2,6-dichloro-3H-pyrido[2,3-d]pyrimidin-4-one (MS: m/e=214.3 [M−H−]) which was used without further purification in the next step.

Workup

  1. extractionThe obtained suspension was extracted with Et2O
  2. customThe water layer was separated
  3. extractionagain extracted (EtOAc)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0d6c2b68be3a472eb0a984d7952c4ad4
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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