Citric Acid → HCID 58201217, compound

HRID 81688Notes

Reaction equation

HRID 81688 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[CH:38]=[CH:37][C:33]([CH2:34][NH:35][NH2:36])=[CH:32][CH:31]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[Cl:26][C:11]1[N:10]=[C:9]([NH2:8])[N:14]=[C:13]2[N:35]([CH2:34][C:33]3[CH:37]=[CH:38][C:30]([O:29][CH3:28])=[CH:31][CH:32]=3)[N:36]=[C:16]([CH2:17][CH:18]3[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]3)[C:12]=12

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 457893744-Methoxybenzylhydrazine hydrochlorideHCID 58201197HCID 58201197, compound

Product 1

HCID 58201217HCID 58201217, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (83.68 ml) was added to a mixture composed of the above 1-(2-amino-4,6-dichloropyrimidin-5-yl)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethan-1-one (61.23 g), (4-methoxybenzyl)-hydrazine hydrochloride (41.50 g) produced by the method described in U.S. Patent No. US2003/18197, and dichloromethane (600 ml) over 30 minutes under cooling in an ice bath. Thereafter, while the temperature of the reaction solution was gradually raised, it was stirred for 17 hours. Thereafter, a 10% citric acid aqueous solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and was then concentrated under reduced pressure. A 5% citric acid aqueous solution was added to the resulting residue, and the precipitate was then collected by filtration. The resultant was washed with water, so as to obtain the title compound (73.84 g) as a solid.

Workup

  1. customproduced by the method
  2. temperatureThereafter, while the temperature of the reaction solution was gradually raised
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationwas then concentrated under reduced pressure
  6. additionA 5% citric acid aqueous solution was added to the resulting residue
  7. filtrationthe precipitate was then collected by filtration
  8. washThe resultant was washed with water

Sources & evidence

ORD record
ord-140ca24a922c4daa9f6421fc75d22130
Source dataset
uspto-grants-2014_09
Patent number
US08846703B2

Reaction notes

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