Hexane → (4,6-Dichloropyrimidin-5-yl)acetaldehyde

HRID 717566Notes

Reaction equation

HRID 717566 reaction equation
[CH2:1]([C:4]1[C:5]([Cl:11])=[N:6][CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=C.C[N+]1([O-])CC[O:16]CC1.CCCCCC>O1CCOCC1.[Os](=O)(=O)(=O)=O>[Cl:11][C:5]1[C:4]([CH2:1][CH:2]=[O:16])=[C:9]([Cl:10])[N:8]=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 82029Methyl morpholine oxideHCID 5192085-Allyl-4,6-dichloropyrimidine

Product 1

HCID 13989292(4,6-Dichloropyrimidin-5-yl)acetaldehydeYield 67.3%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 5-allyl-4,6-dichloropyrimidine (2.5 g) in dry dioxane (25 mL), N-methyl morpholine N-oxide (2.3 g) and osmium tetroxide (0.85 mL, 25% solution in water) were added. The reaction mixture was stirred at room temperature for 2 hours before being quenched by solid sodium bisulphate. The reaction mixture was filtered through celite bed. The celite bed was washed with dioxane (10 mL). The combined filtrate was taken into a 100 mL three necked round bottom flask and sodium metaperiodate (6 g, in 5 mL water) was added. The reaction mixture was stirred at room temperature for about 3 hours, then diluted with water (30 mL). Aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic layer was washed with brine (50 mL) and dried over anhydrous Na2SO4. Evaporation of solvents under reduced pressure gave crude product, which was treated with hexane to offer a solid. The solid obtained was filtered, washed with cold hexane (50 mL) and dried under vacuum to get 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (1.7 g) as white solid. 1H NMR (DMSO-d6): δ 4.21 (s, 2H), 8.86 (s, 1H), 9.7 (s, 1H).

Workup

  1. custombefore being quenched by solid sodium bisulphate
  2. filtrationThe reaction mixture was filtered through celite bed
  3. washThe celite bed was washed with dioxane (10 mL)
  4. additionwas added
  5. stirringThe reaction mixture was stirred at room temperature for about 3 hours
  6. additiondiluted with water (30 mL)
  7. extractionAqueous layer was extracted with dichloromethane (2×25 mL)
  8. washThe combined organic layer was washed with brine (50 mL)
  9. dry with materialdried over anhydrous Na2SO4
  10. customEvaporation of solvents under reduced pressure
  11. customgave crude product, which
  12. customThe solid obtained
  13. filtrationwas filtered
  14. washwashed with cold hexane (50 mL)
  15. customdried under vacuum

Sources & evidence

ORD record
ord-d3d0ead1772a49ff8fb3a8be3fd7291b
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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