Sodium Hydroxide → 2-(p-Pentylphenyl)-5'-propyl-5,2'-bipyrimidinyl

HRID 64586Notes

Reaction equation

HRID 64586 reaction equation
[OH-].[Na+].Cl.[CH2:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]([NH2:23])=[NH:22])=[CH:17][N:16]=2)=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH2:7][CH3:8]>CO>[CH2:4]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]3[N:23]=[CH:14][C:9]([CH2:4][CH2:5][CH3:6])=[CH:10][N:22]=3)=[CH:17][N:16]=2)=[CH:13][CH:14]=1)[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135748272-(p-Pentylphenyl)-5-pyrimidinecarboxamidine hydrochloride

Product 1

HCID 135748282-(p-Pentylphenyl)-5'-propyl-5,2'-bipyrimidinylYield 120%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of NaOH (0.8 g, 0.02 mol) dissolved in dry methanol (30 ml) were added 2-(p-pentylphenyl)-5-pyrimidinecarboxamidine hydrochloride (3.0 g, 0.01 mol) and α-propyl -β-dimethylaminoacrolein (1.4 g, 0.01 mol), followed by boiling with stirring for 2 hours and then distilling off methanol. Water (100 ml) and toluene (100 ml) were added to the reaction residue to extract the product, followed by washing the extraction liquor with water, drying the toluene layer over anhydrous sodium sulfate, distilling off toluene and three times recrystallizing the residual solids from ethanol to obtain the objective 2-(p-pentylphenyl)-5'-propyl-5,2'-bipyrimidinyl (2.0 g, 0.006 mol).

Workup

  1. distillationdistilling off methanol
  2. additionWater (100 ml) and toluene (100 ml) were added to the reaction residue
  3. extractionto extract the product
  4. washby washing the extraction liquor with 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 ethanol

Sources & evidence

ORD record
ord-23484c300d70495cb277f2293b4c3a3c
Source dataset
uspto-grants-1986_09
Patent number
US04609485

Reaction notes

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