Hydrochloric Acid → HCID 178461596, compound

HRID 522806Notes

Reaction equation

HRID 522806 reaction equation
[CH3:1][C@@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:16]=[C:15]2[C:11]([N:12]=[C:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:14]2C2CCCCO2)=[C:10]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@H:30]2[CH3:35])[N:9]=1.Cl.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>C1COCC1>[CH3:1][C@@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:16]=[C:15]2[C:11]([N:12]=[C:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[NH:14]2)=[C:10]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@H:30]2[CH3:35])[N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 895257422,6-Bis-((R)-3-methyl-morpholin-4-yl)-8-pyridin-2-yl-9-(tetrahydro-pyran-2-yl)-9H-purine

Product 1

HCID 178461596HCID 178461596, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-Bis-((R)-3-methyl-morpholin-4-yl)-8-pyridin-2-yl-9-(tetrahydro-pyran-2-yl)-9H-purine (33 mg, 69 μmol) was dissolved in 3 mL of THF. 2N aqueous HCl (344 μl, 688 μmol) was added, and the reaction was stirred for 2 hours at room temperature. 100 mg of Na2CO3 and 10 mL of CH2Cl2 were added, and the reaction mixture was stirred for 20 minutes. The organic layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (12 g SiO2, heptane/EtOAc in a gradient from 100/0 to 3/2) to give the product as a solid (24 mg, 88%).

Workup

  1. stirringthe reaction mixture was stirred for 20 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (12 g SiO2, heptane/EtOAc in a gradient from 100/0 to 3/2)

Sources & evidence

ORD record
ord-38240be343a24e559e05bad977a4e99e
Source dataset
uspto-grants-2016_05
Patent number
US09334271B2

Reaction notes

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