p-Toluenesulfonic acid → HCID 178515252, compound

HRID 334130Notes

Reaction equation

HRID 334130 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:17]3([OH:21])[CH2:20][O:19][CH2:18]3)[N:8]2C2CCCCO2)=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]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]([C:17]3([OH:21])[CH2:20][O:19][CH2:18]3)[NH:8]2)=[C:4]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[N:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86667348HCID 86667348, compound

Product 1

HCID 178515252HCID 178515252, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

3-(2-Chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)oxetan-3-ol (1.8 g, 0.0045 mol) in MeOH (50 mL) was treated with cat. amount of p-toluenesulfonic acid (78 mg, 0.00044 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 3-(2-chloro-6-morpholino-9H-purin-8-yl)oxetan-3-ol (1.2 g, 84% yield). LC/MS (ESI+): m/z 312 (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-a3f9640823b845b186bbaef96576fe49
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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