Hydrochloric Acid → HCID 14397375, compound

HRID 464678Notes

Reaction equation

HRID 464678 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[NH:20][C:19](=[O:21])[C:18]([CH2:22][C:23]2[CH:24]=[N:25][C:26]([CH3:29])=[CH:27][CH:28]=2)=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>N1C=CC=CC=1.O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]2[NH:20][C:19](=[O:21])[C:18]([CH2:22][C:23]3[CH:24]=[N:25][C:26]([CH3:29])=[CH:27][CH:28]=3)=[CH:17][N:16]=2)=[N:3][CH:4]=1)#[N:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 14397373HCID 14397373, compound

Product 1

HCID 14397375HCID 14397375, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2-Chloro-5-cyanopyridine (0.61 g), 2-(3-aminopropylamino)-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone (1.09) and potassium carbonate (0.61 g) were heated together under reflux in pyridine (10 ml) for 2.5 hr. The mixture was stripped, the residue taken up in water and the pH adjusted to 3 with hydrochloric acid. After extracting with chloroform the aqueous solution was filtered and the pH raised to 6.5 with sodium hydroxide. The precipitate thus obtained was chromatographed (silica gel, chloroform/methanol, graded 1:0 to 20:1) and the required component recrystallised twice from ethanol to give 2-[3-(5-cyanopyrid-2-ylamino)propylamino]-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone 0.2H2O, (0.38 g; 25%) m.p. 175°-177° C.

Workup

  1. extractionAfter extracting with chloroform the aqueous solution
  2. filtrationwas filtered
  3. temperaturethe pH raised to 6.5 with sodium hydroxide
  4. customThe precipitate thus obtained
  5. customwas chromatographed (silica gel, chloroform/methanol, graded 1:0 to 20:1)
  6. customthe required component recrystallised twice from ethanol

Sources & evidence

ORD record
ord-c1d6c13c1a02436e8613f10b28dedab0
Source dataset
uspto-grants-1985_10
Patent number
US04548940

Reaction notes

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