Sodium Hydroxide → HCID 135743676, compound

HRID 633695Notes

Reaction equation

HRID 633695 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[N:8]=[C:9]2[NH:17][CH:16]([C:18]([F:21])([F:20])[F:19])[CH2:15][CH2:14][N:10]2[C:11](=[O:13])[CH:12]=1.[OH-].[Na+]>ClCCCl.O.C(OCC)(=O)C>[Cl:3][C:7]1[N:8]=[C:9]2[NH:17][CH:16]([C:18]([F:21])([F:20])[F:19])[CH2:15][CH2:14][N:10]2[C:11](=[O:13])[CH:12]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 135743677HCID 135743677, compound

Product 1

HCID 135743676HCID 135743676, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

136 mL (1440 mmol) of phosphorus oxychloride are added, at room temperature and under an argon atmosphere, to a suspension of 68.10 g (290 mmol) of 2-hydroxy-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one in 950 mL of 1,2-dichloroethane. The mixture obtained is then heated at 65° C. for 3 hours. After cooling, the reaction mixture is evaporated to dryness under reduced pressure. The residue obtained is taken up in 140 mL of cold water and 430 mL of ethyl acetate. 32% sodium hydroxide is added to the mixture obtained, to pH=5. The resulting organic phase is separated out and then dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 60 g of 2-chloro-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one in the form of an orange solid, the characteristics of which are as follows:

Workup

  1. customThe mixture obtained
  2. temperatureAfter cooling
  3. customthe reaction mixture is evaporated to dryness under reduced pressure
  4. customThe residue obtained
  5. customobtained, to pH=5
  6. customThe resulting organic phase is separated out
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d834f068ae8846c5a567323ecf31a4cb
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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