Triethylamine → HCID 59311486, compound

HRID 1693264Notes

Reaction equation

HRID 1693264 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[N:14]=[C:13](Cl)[C:12]([C:16](=O)[CH2:17][CH:18]2[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]2)=[C:11]([Cl:26])[N:10]=1.Cl.[CH3:28][O:29][C:30]1[C:35]([CH3:36])=[CH:34][N:33]=[C:32]([CH2:37][NH:38][NH2:39])[C:31]=1[CH3:40]>ClCCl>[Cl:26][C:11]1[N:10]=[C:9]([NH2:8])[N:14]=[C:13]2[N:38]([CH2:37][C:32]3[C:31]([CH3:40])=[C:30]([O:29][CH3:28])[C:35]([CH3:36])=[CH:34][N:33]=3)[N:39]=[C:16]([CH2:17][CH:18]3[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]3)[C:12]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 58201197HCID 58201197, compoundHCID 67280404HCID 67280404, compound

Product 1

HCID 59311486HCID 59311486, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethylamine (3.44 mL) in dehydrated dichloromethane was added to a mixture composed of 1-(2-amino-4,6-dichloropyrimidin-5-yl)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethan-1-one of 3) above (1.68 g), [(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-hydrazine hydrochloride of 4) above (2.87 g) and dehydrated dichloromethane (60 mL) under cooling in an ice bath over 20 minutes. The ice bath was removed, followed by stirring for two hours. Then, the reaction mixture was separated with chloroform and water. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-chloroform) to obtain the title compound (1.79 g, 75%) as a solid.

Workup

  1. temperatureunder cooling in an ice bath over 20 minutes
  2. customThe ice bath was removed
  3. customThen, the reaction mixture was separated with chloroform and water
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-2c862508a44c4768aee5face3f0bf3f5
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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