Hydrochloric Acid → HCID 178458926, compound

HRID 334159Notes

Reaction equation

HRID 334159 reaction equation
Cl.[Cl:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[C:8]([C:18]([OH:21])([CH3:20])[CH3:19])[N:9]2C2CCCCO2)=[C:5]([Cl:22])[N:4]=1>C(Cl)Cl.CO>[Cl:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[C:8]([C:18]([OH:21])([CH3:20])[CH3:19])[NH:9]2)=[C:5]([Cl:22])[N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866673692-[2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-8-purinyl]-2-propanol

Product 1

HCID 178458926HCID 178458926, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

HCl (5 mL, 5 mmol, 1 M aqueous solution) was added to a solution of 2-[2,6-dichloro-9-(tetrahydro-pyran-2-yl)-9H-purin-8-yl]-propan-2-ol (6.0 g, 20.66 mmol) in a mixture of DCM (15 mL) and methanol (15 mL) and the resulting solution stirred at RT for 1 h, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0 to 50% methanol in DCM) affording 2-(2,6-Dichloro-9H-purin-8-yl)-propan-2-ol as a dark solid (3.38 g, 66%). LCMS (method A): RT=2.12 min, [M−H]=245/247. 1H NMR (400 MHz, CDCl3): δ 1.50 (6H, s)

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, gradient 0 to 50% methanol in DCM)

Sources & evidence

ORD record
ord-f2a3272180ac40d490f3670418b0e6d2
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

Loading…