Hydrochloric Acid → HCID 178447855, compound

HRID 1589754Notes

Reaction equation

HRID 1589754 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:20]=C[C:18]([C@H:21]4[CH2:26][CH2:25][C@H:24]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[CH:11][N:10]=2)=[CH:4][C:3]=1[F:30].[Cu][C:32]#[N:33].[CH3:34]N1C(=O)CCC1.Cl>O>[C:32]([C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:34][C:18]([C@H:21]4[CH2:22][CH2:23][C@H:24]([CH2:27][CH2:28][CH3:29])[CH2:25][CH2:26]4)=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:4][C:3]=1[F:30])#[N:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 178418546HCID 178418546, compoundHCID 178447854HCID 178447854, compound

Product 1

HCID 178447855HCID 178447855, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

3.0 g (0.006 mol) of 2-(4'-bromo-3',5'-difluorophenyl)-5-[4'-(trans-4"-propylcyclohexyl)phenyl]pyrimidine and 0.8 g (0.08 mol) of copper (I) cyanide were added to 30 cm3 of NMP and the solution was refluxed for 2 hours using a mantle heater. The solution was cooled to 60° C. and added to a solution of 3.2 g of FeC13.6H2O, 1.0 cm3 of concentrated hydrochloric acid and 4 cm3 of water. The resulting solution was allowed to sit on a warm water bath at 60° C. for one hour. The crystals formed were filtered out, washed with water and treated through a silica gel column using chloroform as the solvent. The chloroform was distilled off and the residue was recrystallized from a solvent mixture of acetone and chloroform to yield 1.3 g (0.003 mol) of 2-(4'-cyano-3',5'-difluorophenyl)-5-[4 '-(trans-4"-propylcyclohexyl)phenyl]pyrimidine. The phase transition temperature of this compound, as measured by DSC, was: ##STR36##

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. customThe crystals formed
  3. filtrationwere filtered out
  4. washwashed with water
  5. additiontreated through a silica gel column
  6. distillationThe chloroform was distilled off
  7. customthe residue was recrystallized from a solvent mixture of acetone and chloroform

Sources & evidence

ORD record
ord-6ca646149e2b46329f63a028c473eba8
Source dataset
uspto-grants-1993_04
Patent number
US05200110

Reaction notes

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