Hydrochloric Acid → 4-Chloro-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine

HRID 1693320Notes

Reaction equation

HRID 1693320 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.Cl>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 313Hydrochloric AcidHCID 8471TriethylamineHCID 457893744-Methoxybenzylhydrazine hydrochlorideHCID 58201197HCID 58201197, compound

Product 1

HCID 582012174-Chloro-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amineYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethylamine (29.1 ml) in dichloromethane (100 ml) 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 (16 g), (4-methoxybenzyl)-hydrazine hydrochloride (14.1 g) and dichloromethane (400 ml) under cooling in an ice bath over 15 minutes. After stirring under cooling in an ice bath for 1.5 hours, a 0.2 N hydrochloric acid solution (1000 ml) was added to the reaction mixture, followed by extraction with dichloromethane (400 ml). The organic layer was washed with brine (500 ml) and 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 (16.5 g, 78%) as a solid.

Workup

  1. temperatureunder cooling in an ice bath over 15 minutes
  2. temperatureunder cooling in an ice bath for 1.5 hours
  3. extractionfollowed by extraction with dichloromethane (400 ml)
  4. washThe organic layer was washed with brine (500 ml)
  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-5c1716f26ed64b9b998a4378e701eeef
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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