Water → 3-(4,6-Dimethylpyrimid-2-ylamino)propane-1,2-diol

HRID 52397Notes

Reaction equation

HRID 52397 reaction equation
C[N+]1([O-])CC[O:5]CC1.[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([NH:17][CH2:18][CH:19]=[CH2:20])[N:11]=1.S([O-])(O)=O.[Na+].[OH2:26]>CC(C)=O.[Os](=O)(=O)(=O)=O>[CH3:16][C:14]1[CH:15]=[C:10]([CH3:9])[N:11]=[C:12]([NH:17][CH2:18][CH:19]([OH:5])[CH2:20][OH:26])[N:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 133866534,6-Dimethyl-N-(prop-2-en-1-yl)pyrimidin-2-amineHCID 23665763Sodium Bisulfite

Product 1

HCID 199636663-(4,6-Dimethylpyrimid-2-ylamino)propane-1,2-diol

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent2×

Procedure

N-methylmorpholine-N-oxide (64.0 g, 0.47 mol) and osmiumtetroxide (0.7 g, 2.75 mmol) were dissolved in a mixture of 180 ml water and 100 ml acetone. 1-(4,6-dimethylpyrimid-2-ylamino)-prop-2-ene (73.5 g, 0.45 mol) in 100 ml acetone was added over a period of 15 minutes. The mixture was stirred at room temperature for 1 hour and then warmed to 50° C. for 2 hours. 10 ml aqueous saturated sodium hydrogensulphite was then added together with 40 g of diatomaceous earth. After filtration the reaction mixture was evaporated to dryness and the residue extracted with dioxane/ethanol 2:1 (700 ml). Filtration from insoluble material and concentration of the solution in vacuum caused crystallisation of the product. Addition of toluene completed product precipitation, which was isolated by filtration (83 g, m.p. 124°-127° C.).

Workup

  1. temperaturewarmed to 50° C. for 2 hours
  2. filtrationAfter filtration the reaction mixture
  3. customwas evaporated to dryness
  4. extractionthe residue extracted with dioxane/ethanol 2:1 (700 ml)
  5. filtrationFiltration from insoluble material and concentration of the solution in vacuum
  6. customcrystallisation of the product
  7. additionAddition of toluene completed product precipitation
  8. customwhich was isolated by filtration (83 g, m.p. 124°-127° C.)

Sources & evidence

ORD record
ord-ba290f6afe534fd59b6ee6ad002bde38
Source dataset
uspto-grants-1997_04
Patent number
US05616708

Reaction notes

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