Pyridine-4-amidine hydrochloride → 5-(4-Chlorophenyl)-2-pyridin-4-ylpyrimidine

HRID 393740Notes

Reaction equation

HRID 393740 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH:11]1[C:16]([CH:17]([CH:20]=O)[CH:18]=O)=[CH:15][CH:14]=[C:13]([Cl:22])[CH:12]=1>N1C=CC=CC=1>[Cl:22][C:13]1[CH:14]=[CH:15][C:16]([C:17]2[CH:18]=[N:9][C:2]([C:3]3[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=3)=[N:10][CH:20]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 2776844Pyridine-4-amidine hydrochlorideHCID 35843862-(4-Chlorophenyl)malonaldehyde

Product 1

HCID 226467355-(4-Chlorophenyl)-2-pyridin-4-ylpyrimidineYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Isonicotinamidine, hydrochloride (0.488 g) and 2-(4-chlorophenyl)malondialdehyde (0.566 g) were combined in anhydrous pyridine (10 ml) and heated to reflux under nitrogen, for 18 h. The resultant dark solution was cooled and poured onto ice-water (150 ml) and the mixture extracted with ethyl acetate (150 ml, then 50 ml). The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml), dried (Na2SO4), evaporated to dryness under reduced pressure and the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent, to give the title compound as a white solid (0.463 g, 56%).

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen, for 18 h
  3. temperatureThe resultant dark solution was cooled
  4. additionpoured onto ice-water (150 ml)
  5. extractionthe mixture extracted with ethyl acetate (150 ml
  6. washThe combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated to dryness under reduced pressure
  9. customthe residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent

Sources & evidence

ORD record
ord-c7ec062d1aae491882e14fec13f2a0c4
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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