5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one → Temelastine

HRID 1153738

Reaction equation

HRID 1153738 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH: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>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][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:6][CH:7]=1

Participants

4

Reactant 2

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamine

Product 1

HCID 55482TemelastineYield 63.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-(4-aminobutyl)-3-methylpyridine (2.12 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone (3.18 g) were refluxed in pyridine (12 ml) for 9.5 hrs. The pyridine was removed in vacuo and the residue was re-evaporated with n-propanol (2×50 ml), triturated with chloroform, filtered and the solution was chromatographed on silica in chloroform-methanol (10:1). The product was crystallised from ethanol-ether to give 2-[4-(5-bromo-3-methylpyrid-2-yl)-butylamino]-5-(6-methylpyrid-3-yl-methyl)-4-pyrimidone (2.44 g) m.p. 151°-152° C.

Workup

  1. customThe pyridine was removed in vacuo
  2. customthe residue was re-evaporated with n-propanol (2×50 ml)
  3. customtriturated with chloroform
  4. filtrationfiltered
  5. customthe solution was chromatographed on silica in chloroform-methanol (10:1)
  6. customThe product was crystallised from ethanol-ether

Sources & evidence

ORD record
ord-ac812736d4c743b6a92d8809a65a9492
Source dataset
uspto-grants-1984_12
Patent number
US04486434

Linked notes

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