Triethylamine → HCID 59020423, compound

HRID 970444Notes

Reaction equation

HRID 970444 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)=[O:7].[Br:18][C:19]1[C:20](Cl)=[N:21][C:22]([Cl:25])=[N:23][CH:24]=1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[Br:18][C:19]1[C:20]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[O:7])=[N:21][C:22]([Cl:25])=[N:23][CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 59020410HCID 59020410, compound

Product 1

HCID 59020423HCID 59020423, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.6 g (6.7 mmol) of 1-(3-amino-propyl)-3-(3-nitro-phenyl)-urea in 30 ml of acetonitrile is mixed with a solution of 1.6 g (7.0 mmol) of 5-bromo-2,4-dichloro-pyrimidine in 10 ml of acetonitrile. 2.0 ml of triethylamine is added, and it is stirred for 90 minutes at room temperature. It is diluted with ethyl acetate (150 ml) and washed with citric acid (10%), saturated NaHCO3 solution as well as saturated NaCl solution, dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate 1:1). 1.7 g (4.0 mmol, corresponding to 60% of theory) of the product is obtained.

Workup

  1. washwashed with citric acid (10%), saturated NaHCO3 solution as well as saturated NaCl solution
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe remaining residue is purified by chromatography (hexane/ethyl acetate 1:1)
  6. custom1.7 g (4.0 mmol, corresponding to 60% of theory) of the product is obtained

Sources & evidence

ORD record
ord-cb0200b9910342c0a4168edf419c00bc
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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