Ethanol → HCID 88659347, compound

HRID 1906547Notes

Reaction equation

HRID 1906547 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[CH:8][N:7]=1.[N+]([NH:19][C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:29]=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=2)=[CH:22][N:21]=1)([O-])=O.C(O)C>N1C=CC=CC=1>[OH2:14].[CH3:12][C:11]1[C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:20]2[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]3[CH:29]=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=3)=[CH:22][N:21]=2)=[N:7][CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=1.[CH3:12][C:11]1[C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:19][C:20]2[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]3[CH:29]=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=3)=[CH:22][N:21]=2)=[N:7][CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 14397366HCID 14397366, compound

Product 1

HCID 88659347HCID 88659347, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(3-Aminopropylamino)-3-methyl-5-nitropyridine, (1.58 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone (1.44 g) were heated together under reflux in pyridine (3 ml) for 22 hr. On cooling, the mixture was treated with ethanol and a mustard coloured solid filtered off (1.88 g,) m.p. 166°-68° C. Recrystallisation from dimethyl formamide/ethanol and finally twice from dimethyl formamide/water gave 2-[3-(3-methyl-5-nitropyrid-2-ylamino)propylamino]-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone hemihydrate (1.67 g; 74%) m.p. 110° C. (softens).

Workup

  1. temperatureOn cooling
  2. filtrationfiltered off (1.88 g,) m.p. 166°-68° C
  3. customRecrystallisation from dimethyl formamide/ethanol

Sources & evidence

ORD record
ord-d70fec64d62d4fb08b8a51e008ba1105
Source dataset
uspto-grants-1987_03
Patent number
US04652650

Reaction notes

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