Ethanol → HCID 131710700, compound

HRID 597469Notes

Reaction equation

HRID 597469 reaction equation
C([N:3](CC)CC)C.Cl[C:9]1C=[C:13](Cl)[C:12]([N+:16]([O-:18])=[O:17])=[C:11]([CH:19]([CH3:21])[CH3:20])[N:10]=1.[NH2:22][CH:23](CC)[CH2:24][CH3:25].[CH2:28](O)[CH3:29]>>[CH2:23]([NH:22][N:3]1[CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:11]([CH:19]([CH3:20])[CH3:21])=[N:10][CH2:9]1)[CH2:24][CH2:25][CH2:28][CH3:29]

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 120193-PentanamineHCID 21445107HCID 21445107, compound

Product 1

HCID 131710700HCID 131710700, compound

Conditions

Temperature
20 °C

Procedure

20.2 g (0.2 mole) of triethylamine are added to 47.2 g (0.2 mole) of 2,4-dichloro-5-nitro-6-isopropyl-pyridine in 1 liter of ethanol and 17.5 g (0.2 mole) of 3-aminopentane are added dropwise at -20° C. The reaction mixture is stirred overnight at 20° C and then concentrated. The residue is suspended in water and extracted with ether. The ethereal extracts are drid over MgSO4 and evaporated. The product is purified by adsorption chromatography on silica gel by elution with benzene to yield 48 g of 2-chloro-4-(3-pentylamino-5-nitro-6-isopropyl-pyrimidine (nD20 : 1.5478).

Workup

  1. additionare added dropwise at -20° C
  2. concentrationconcentrated
  3. extractionextracted with ether
  4. customevaporated
  5. customThe product is purified by adsorption chromatography on silica gel by elution with benzene

Sources & evidence

ORD record
ord-c4cabf65134f4e46bd0e4cd78c0d77de
Source dataset
uspto-grants-1977_03
Patent number
US04014677

Reaction notes

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