Water → HCID 86714786, compound

HRID 2171932Notes

Reaction equation

HRID 2171932 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH2:14][CH:15]=[CH2:16])[C:10]([CH3:13])([CH3:12])[CH3:11])[C:5]([F:17])=[CH:4][N:3]=1.C[N+]1([O-])CC[O:22]CC1.[OH2:26]>C1COCC1.[O-]S([O-])(=S)=O.[Na+].[Na+].[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH:15]([OH:22])[CH2:16][OH:26])[C:5]([F:17])=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 86714784HCID 86714784, compound2×

Product 1

HCID 86714786HCID 86714786, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of (R)-2-chloro-N-(2,2-dimethylhex-5-en-3-yl)-5-fluoropyrimidin-4-amine, 188a, (0.140 g, 0.543 mmol) in THF (10 mL) and H2O (10 mL) was added osmium tetraoxide (0.138 g, 0.014 mmol) and 4-methylmorpholine-4-oxide (0.085 mL, 0.815 mmol). The reaction mixture was stirred at room temperature for 2.5 hours. The mixture was diluted with aqueous saturated Na2S2O3. The resulting mixture was stirred for 20 minutes and extracted with EtOAc. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (MeOH/CH2Cl2) to afford 90 mg of the first diastereomer, 189a, and 65 mg of the second diastereomer, 190a.

Workup

  1. stirringThe resulting mixture was stirred for 20 minutes
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-90e5176b149f40fca0bb9520818703c3
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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