Ammonia → 2-(p-Cyanophenyl)-5'-pentyl-5,2'-bipyrimidinyl

HRID 64588Notes

Reaction equation

HRID 64588 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:16][N:15]=3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:25][N:26]1CCCC1=O.N>C1(C)C=CC=CC=1>[C:25]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:16][N:15]=3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1)#[N:26]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 135875282-(p-Bromophenyl)-5'-pentyl-5,2'-bipyrimidinyl

Product 1

HCID 135875292-(p-Cyanophenyl)-5'-pentyl-5,2'-bipyrimidinyl

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-(p-bromophenyl)-5'-pentyl-5,2'-bipyrimidinyl (5.0 g, 0.013 mol), N-methyl-2-pyrrolidone (100 mL) and cuprous cyanide (1.16 g, 0.013 mol) was heated under reflux for 5 hours, followed by cooling the reaction mixture down to 40° C., adding toluene (500 ml) and 28% aqueous ammonia (100 ml), separating the resulting layers, washing the toluene layer with water till the washing water became neutral, drying the toluene layer over anhydrous sodium sulfate, distilling off toluene, and three times recrystallizing the residual solids from toluene to obtain 2-(p-cyanophenyl)-5'-pentyl-5,2'-bipyrimidinyl (2.1 g, 0.006 mol).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customseparating the resulting layers
  4. washwashing the toluene layer with water till the washing water
  5. dry with materialdrying the toluene layer over anhydrous sodium sulfate
  6. distillationdistilling off toluene, and three times
  7. customrecrystallizing the residual solids from toluene

Sources & evidence

ORD record
ord-90e105e3aaa24b80a2491e24929b2b56
Source dataset
uspto-grants-1986_09
Patent number
US04609485

Reaction notes

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