2-Pyrrolidone → HCID 86659383, compound

HRID 2043404Notes

Reaction equation

HRID 2043404 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][C:20]1=[O:24].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[Cl:8][C:6]1[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=[C:2]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:24])[CH:7]=1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 62657Potassium Phosphate, TribasicHCID 86659372(S)-4,6-Dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidin-2-amine

Product 1

HCID 86659383HCID 86659383, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

100 mg of (S)-4,6-dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidine-2-amine (Reference Example 1), 33 mg of 2-pyrrolidone, 20 mg of 4,5-bis(diphenylphosphino)-9,9′-dimethylxanthene, 149 mg of tripotassium phosphate and 19 mg of tris(dibenzylideneacetone)(chloroform)dipalladium were added in turn to 3 ml of degassed 1,4-dioxane, and the mixture was stirred at 100° C. for 3 hours under argon atmosphere. The reaction solution was filtrated to remove precipitates, and the solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 106 mg of the objective compound as yellow oil.

Workup

  1. filtrationThe reaction solution was filtrated
  2. customto remove
  3. customprecipitates
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9d551212c684412cb82aaea0e5b0854b
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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