p-Toluenesulfonic acid → HCID 178519941, compound

HRID 334148Notes

Reaction equation

HRID 334148 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[N:8]2C2CCCCO2)=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]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]([CH:17]([OH:22])[C:18]([F:19])([F:21])[F:20])[NH:8]2)=[C:4]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[N:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86667364HCID 86667364, compound

Product 1

HCID 178519941HCID 178519941, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1-(2-Chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)-2,2,2-trifluoroethanol (1.3 g, 0.0031 mol) in MeOH (12 mL) was treated with cat. amount of p-toluenesulfonic acid (53 mg, 0.00031 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 1-(2-chloro-6-morpholino-9H-purin-8-yl)-2,2,2-trifluoroethanol (1 g, 100% yield). LC/MS (ESI+): m/z 338 (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-c1f31b3b2c2944d39a8f9574c2080b2c
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

Loading…