p-Toluenesulfonic acid → HCID 178519940, compound

HRID 334128Notes

Reaction equation

HRID 334128 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:17][OH:18])[N:8]2C2CCCCO2)=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:17][OH:18])[NH:8]2)=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86667346(2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)methanol

Product 1

HCID 178519940HCID 178519940, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

(2-Chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)methanol (3.4 g, 0.0096 mol) in MeOH (20 mL) was treated with a catalytic amount of p-toluenesulfonic acid (0.25 g, 0.00144 mol). The reaction mixture was heated to 50° C. overnight and was then concentrated under reduce pressure. The residue was partitioned between water and EtOAc. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated to dryness to give (2-chloro-6-morpholino-9H-purin-8-yl)methanol (2.6 g, 100% yield). LC/MS (ESI+): m/z 271 (M+H)

Workup

  1. concentrationwas then concentrated
  2. customThe residue was partitioned between water and EtOAc
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-66d8a3707147476c965f90a8f7c94c97
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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