Hydrochloric Acid → HCID 71239062, compound

HRID 1774615Notes

Reaction equation

HRID 1774615 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]=[CH:4][N:3]=1.[NH:16]1[CH2:23][CH2:22][CH2:21][C@@H:17]1[C:18]([OH:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].Cl>CC(N(C)C)=O.C(OCC)(=O)C.[Cu]I>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([N:16]3[CH2:23][CH2:22][CH2:21][C@@H:17]3[C:18]([OH:20])=[O:19])[CH:7]=2)[CH:13]=[CH:12][C:11]=1[Cl:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8988D-ProlineHCID 11430Potassium CarbonateHCID 24902229HCID 24902229, compound

Product 1

HCID 71239062HCID 71239062, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

4-Chloro-6-(3,4-dichloro-phenyl)-pyrimidine (0.3 g, 1.2 mmol) and D-proline (0.13 g, 1.2 mmol) were added in one portion to a pressure vessel containing a solution of copper (I) Iodide (0.02 g, 0.16 mmol) and potassium carbonate (0.24 g, 1.8 mmol) in DMA (5 ml). The vessel was sealed and heated at 90° C. for 16 hours before being cooled to room temperature. The mixture was cooled to room temperature, diluted with ethyl acetate (10 ml) and acidified to pH 1 with concentrated HCl. The mixture was extracted with ethyl acetate (3×30 ml) and the organic layers were combined, dried (MgSO4), filtered, concentrated and the resulting residue was purified by prep HPLC to give the title compound (0.17 g, 43% yield) as a white solid.

Workup

  1. customThe vessel was sealed
  2. temperaturebefore being cooled to room temperature
  3. temperatureThe mixture was cooled to room temperature
  4. extractionThe mixture was extracted with ethyl acetate (3×30 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe resulting residue was purified by prep HPLC

Sources & evidence

ORD record
ord-007eaa7693f44da9b46130e3502cbcfe
Source dataset
uspto-grants-2016_02
Patent number
US09260422B2

Reaction notes

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