Hydrochloric Acid → HCID 178447853, compound

HRID 1589750Notes

Reaction equation

HRID 1589750 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C@H:20]4[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)=[CH:10][N:9]=2)=[CH:4][C:3]=1[F:29].[Cu][C:31]#[N:32].CN1C(=O)CCC1.Cl>O>[C:31]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([C:14]3[CH:15]=[CH:16][C:17]([C@H:20]4[CH2:21][CH2:22][C@H:23]([CH2:26][CH2:27][CH3:28])[CH2:24][CH2:25]4)=[CH:18][CH:19]=3)=[CH:12][N:13]=2)=[CH:4][C:3]=1[F:29])#[N:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 178418546HCID 178418546, compoundHCID 178447851HCID 178447851, compound

Product 1

HCID 178447853HCID 178447853, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

3.5 g (0.008 mol) of 2-(4'-bromo-3'-fluorophenyl)-5-[4'-(trans-4"-propylcyclohexyl)phenyl]pyrimidine and 1.1 g (0.012 mol) of copper (I) cyanide were added to 31 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 4.2 g of FeC13.6H2 o, 1.3 cm3 of concentrated hydrochloric acid and 6 cm3 of water. The resulting solution was maintained on a warm water bath at 60° C. for one hour. The crystals deposited were filtered, washed with water and treated through a silica gel column with chloroform as the solvent. The chloroform was distilled off and the residue was recrystallized from acetone to yield 1.9 g (0.005 mol) of 2-(4'-cyano-3'-fluorophenyl)-5-[4'-(trans-4"-propylcyclohexyl)phenyl]pyrimidine. The phase transition temperature of this compound measured by DSC, was: ##STR32##

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. temperatureThe resulting solution was maintained on a warm water bath at 60° C. for one hour
  3. filtrationThe crystals deposited were filtered
  4. washwashed with water
  5. additiontreated through a silica gel column with chloroform as the solvent
  6. distillationThe chloroform was distilled off
  7. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-f4629627ee8344818fa0a415f4e0de23
Source dataset
uspto-grants-1993_04
Patent number
US05200110

Reaction notes

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