Diisopropylethylamine → HCID 178461592, compound

HRID 522801Notes

Reaction equation

HRID 522801 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4](Cl)[N:3]=1.Cl.[CH3:13][C@@H:14]1[CH2:19][O:18][CH2:17][CH2:16][NH:15]1.C(N(C(C)C)CC)(C)C>C(O)(C)C.C(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][C@H:14]2[CH3:13])[N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 57356922(3R)-3-Methylmorpholine hydrochlorideHCID 1784188752,6-dichloro-1H-purine

Product 1

HCID 178461592HCID 178461592, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

2,6-Dichloro-9H-purine (2.36 g, 12.5 mmol), (R)-3-methylmorpholin hydrochloride (1.89 g, 13.8 mmol), and diisopropylethylamine (5.46 mL, 31.3 mmol) were dissolved in 15 mL of isopropanol, and the reaction mixture was stirred for 18 hours at 75° C. The reaction mixture was then diluted with 200 mL of CH2Cl2. The organic solvents were washed with aqueous Na2CO3, followed by water and brine. Drying over Na2SO4, filtering and concentration under reduced pressure gave a residue, which was purified by column chromatography (150 g SiO2, CH2Cl2/EtOH/aq NH3 in a ratio of 96/4/0.1) to give the product as a solid (2.87 g, 91%).

Workup

  1. washThe organic solvents were washed with aqueous Na2CO3
  2. dry with materialDrying over Na2SO4
  3. filtrationfiltering
  4. concentrationconcentration under reduced pressure
  5. customgave a residue, which
  6. customwas purified by column chromatography (150 g SiO2, CH2Cl2/EtOH/aq NH3 in a ratio of 96/4/0.1)

Sources & evidence

ORD record
ord-96f55633c3ba4c54b37d56e267289d66
Source dataset
uspto-grants-2016_05
Patent number
US09334271B2

Reaction notes

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