Hydrochloric Acid → HCID 14397387, compound

HRID 1906548Notes

Reaction equation

HRID 1906548 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-1e22c00561f84f73915c73c40f2971fc
Source dataset
uspto-grants-1987_03
Patent number
US04652650

Reaction notes

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