Hydrochloric Acid → HCID 14397387, compound

HRID 464682Notes

Reaction equation

HRID 464682 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][N:7]=1.[N+](N[C:18]1[NH:23][C:22](=[O:24])[C:21]([CH2:25][C:26]2[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=2)=[CH:20][N:19]=1)([O-])=O.C(Cl)(Cl)Cl.Cl>O>[CH3:12][C:11]1[C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:18]2[NH:23][C:22](=[O:24])[C:21]([CH2:25][C:26]3[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=3)=[CH:20][N:19]=2)=[N:7][CH:8]=[C:9]([CH3:13])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 14397363N1-(3,5-Dimethyl-2-pyridinyl)-1,3-propanediamine

Product 1

HCID 14397387HCID 14397387, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(3-Aminopropylamino)-3,5-dimethylpyridine (0.81 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone (1.04 g) were fused together on an oil bath at 140° C. for 6 hr. On cooling the resulting mixture was equilibrated between chloroform and water (pH adjusted to 5.5 with dil. hydrochloric acid). The pH of the aqueous solution was raised to 6.5 and the product extracted out with chloroform. After drying (MgSO4) and stripping, recrystallisation from ethyl acetate and finally twice from ethanol/water gave 2-[3-(3,5-dimethylpyrid-2-ylamino)propylamino]-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone 2.4H2O, (0.83 g; 49%) m.p. 104°-5° C. (softens ca 90° C.).

Workup

  1. temperatureOn cooling the resulting mixture
  2. temperatureThe pH of the aqueous solution was raised to 6.5
  3. extractionthe product extracted out with chloroform
  4. dry with materialAfter drying (MgSO4)
  5. customrecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-ce42a3352fe9428c8d6adcb8c65febc9
Source dataset
uspto-grants-1985_10
Patent number
US04548940

Reaction notes

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