Sodium Chloride → HCID 54017983, compound

HRID 2416412Notes

Reaction equation

HRID 2416412 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]([CH3:10])[C:8](=[O:11])[NH:7][C:6](=[O:12])[CH:5]=1.[H][H].[C:15]([O:18][C@H:19]([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23]Cl)(=[O:17])[CH3:16].[Cl-].[Na+]>CS(C)=O>[C:15]([O:18][C@H:19]([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][N:7]1[C:6](=[O:12])[CH:5]=[C:4]([NH2:3])[N:9]([CH3:10])[C:8]1=[O:11])(=[O:17])[CH3:16]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 755206-Amino-1-methyluracilHCID 110194345-(R)-Acetoxy-1-chlorohexaneHCID 178418361HCID 178418361, compound

Product 1

HCID 54017983HCID 54017983, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 1 liter round bottomed flask was charged with 95% sodium hydride (5.5 g, 220 mmol), dry dimethylsulfoxide (400 ml), and was cooled in an ice bath. 6-Amino-1-methyluracil (28.2 g, 200 mmol) was added slowly in portions. After evolution of hydrogen gas had subsided, the mixture was warmed to room temperature and stirred until the solid had completely dissolved (1 hour). (R)-5-Acetoxy-1-chlorohexane (37.5 g, 210 mmol), prepared as described by Klein, J. P.; Leigh, A. J.; Michnick, J.; Kumar, A. M.; Underiner, G. E. Asymmetric Synthesis of Chiral Secondary Alcohols, U.S. Pat. No. 5,629,423 (May 13, 1997), was added slowly. The mixture was heated at 80° C. for 18 hours, and after cooling to room temperature, was treated with saturated aqueous sodium chloride solution (1 L) and extracted with ethyl acetate (4×200 ml). The combined extracts were washed again with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was treated with diethyl ether (100 ml) and stirred for 18 hours. The solid was filtered, rinsed with diethyl ether, and dried under vacuum to provide (R)-3-(5-acetoxyhexyl)-6-amino-1-methyluracil (37 g, 65% yield) as a beige powder. 1H NMR (300 MHz, CDCl3) δ 1.17 (d, 3H), 1.25-1.71 (m, 6H), 2.00 (s, 3H), (t, 2H), 4.75-4.90 (m, 3H), 4.95 (s, 1H).

Workup

  1. temperaturewas cooled in an ice bath
  2. dissolutionhad completely dissolved (1 hour)
  3. addition5,629,423 (May 13, 1997), was added slowly
  4. temperatureThe mixture was heated at 80° C. for 18 hours
  5. temperatureafter cooling to room temperature
  6. extractionextracted with ethyl acetate (4×200 ml)
  7. washThe combined extracts were washed again with saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionThe residue was treated with diethyl ether (100 ml)
  11. stirringstirred for 18 hours
  12. filtrationThe solid was filtered
  13. washrinsed with diethyl ether
  14. customdried under vacuum

Sources & evidence

ORD record
ord-80a3fe9921824441b4a4c321330b3a64
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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