Hydrochloric Acid → HCID 14397397, compound

HRID 1906552Notes

Reaction equation

HRID 1906552 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([Cl:14])=[CH:9][N:8]=1.[N+](N[C:19]1[NH:24][C:23](=[O:25])[C:22]([CH2:26][C:27]2[CH:28]=[N:29][C:30]([CH3:33])=[CH:31][CH:32]=2)=[CH:21][N:20]=1)([O-])=O.Cl>O>[Cl:14][C:10]1[CH:11]=[C:12]([CH3:13])[C:7]([NH:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:19]2[NH:24][C:23](=[O:25])[C:22]([CH2:26][C:27]3[CH:28]=[N:29][C:30]([CH3:33])=[CH:31][CH:32]=3)=[CH:21][N:20]=2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 14397372HCID 14397372, compound

Product 1

HCID 14397397HCID 14397397, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(4-Aminobutylamino)-5-chloro-3-methylpyridine (1.81 g) and 2-nitroamino-5-(6-methylpyrid-3ylmethyl)-4-pyrimidone (1.95 g) were fused together on an oil bath at 140°-50° C. for 2 hr. On cooling the mixture was treated with water and dilute hydrochloric acid and some solid material removed at pH 4. On raising the pH to 5 a precipitate was obtained which on recrystallising twice from dimethyl formamide/water gave 2-[4-(5-chloro-3-methylpyrid-2-ylamino)butylamino]-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone (1.2 g; 39%) m.p. 202°-3° C.

Workup

  1. temperatureOn cooling the mixture
  2. customsome solid material removed at pH 4
  3. temperatureOn raising the pH to 5 a precipitate
  4. customwas obtained which
  5. customon recrystallising twice from dimethyl formamide/water

Sources & evidence

ORD record
ord-35e0f0b031ac475bb129e16982cf678e
Source dataset
uspto-grants-1987_03
Patent number
US04652650

Reaction notes

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