Tetrahydrofuran → 1-{4-Chloro-6-[2-(2,4-dichloro-phenyl)-ethylamino]-pyrimidin-2-yl}-ethane-1,2-diol

HRID 216242Notes

Reaction equation

HRID 216242 reaction equation
[Cl:1][C:2]1[N:7]=C(C=C)[N:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH:3]=1.C[N+]1([O-])CC[O:25]CC1.S(=O)(O)[O-].[Na+].[CH2:34]1C[O:37][CH2:36][CH2:35]1>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[N:5]=[C:34]([CH:35]([OH:25])[CH2:36][OH:37])[N:7]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 86240105(6-Chloro-2-vinyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine

Product 1

HCID 866157091-{4-Chloro-6-[2-(2,4-dichloro-phenyl)-ethylamino]-pyrimidin-2-yl}-ethane-1,2-diol

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of (6-chloro-2-vinyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine (240 mg, 0.73 mmol) in THF (2 mL), acetone (2 mL) and water (2 mL) is added 4-methylmorpholine N-oxide (342 mg, 2.92 mmol) followed by osmium tetroxide (153 μL, 0.015 mmol). After stirring the mixture at room temperature for 17 hours a solution of sodium bisulfite (728 mg, 7 mmol) in water (15 mL) is added and extracted twice with EtOAc (25 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford 1-{4-chloro-6-[2-(2,4-dichloro-phenyl)-ethylamino]-pyrimidin-2-yl}-ethane-1,2-diol (320 mg) as a solid.

Workup

  1. additionis added
  2. extractionextracted twice with EtOAc (25 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c012dc8bb9174450a40a7daf5716586d
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

Loading…