Sodium Chloride → HCID 58467965, compound

HRID 1027853Notes

Reaction equation

HRID 1027853 reaction equation
[H-].[Na+].[CH3:3][C:4]([OH:9])([C@H:6]([OH:8])[CH3:7])[CH3:5].[Cl:10][C:11]1[N:16]=[C:15](Cl)[C:14]([I:18])=[CH:13][N:12]=1.[Na+].[Cl-]>C(OCC)C.C(#N)C>[Cl:10][C:11]1[N:16]=[C:15]([O:8][C@H:6]([CH3:7])[C:4]([CH3:5])([OH:9])[CH3:3])[C:14]([I:18])=[CH:13][N:12]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 2634382,4-Dichloro-5-iodopyrimidineHCID 12328294(3R)-2-Methylbutane-2,3-diol

Product 1

HCID 58467965HCID 58467965, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

1.84 g (42.3 mmol) of sodium hydride (55%) was added in portions, with stirring at 0° C., to a solution of 4.40 g (42.3 mmol) (R)-2-methyl-butane-2,3-diol in 83 ml diethyl ether and was stirred for 10 minutes. It was stirred for a further 3 minutes at room temperature and the mixture was then added to an ice-cooled solution of 9.68 g (35.2 mmol) of 2,4-dichloro-5-iodo-pyrimidine in 97 ml acetonitrile. The mixture was stirred for 4 hours at 40° C. and, after cooling, ice and saturated NaCl solution were added. It was then extracted with ethyl acetate (3×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was purified chromatographically (hexane/ethyl acetate 4:1). 4.96 g (14.5 mmol; yield: 41%) of the product was obtained.

Workup

  1. stirringIt was stirred for a further 3 minutes at room temperature
  2. stirringThe mixture was stirred for 4 hours at 40° C.
  3. temperatureafter cooling
  4. extractionIt was then extracted with ethyl acetate (3×)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customThe residue obtained
  9. customwas purified chromatographically (hexane/ethyl acetate 4:1)
  10. custom4.96 g (14.5 mmol; yield: 41%) of the product was obtained

Sources & evidence

ORD record
ord-c8cc9c514e004f46b74ab6172f7efe3c
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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