Triethylamine → HCID 58201197, compound

HRID 1693262Notes

Reaction equation

HRID 1693262 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[N:14]=[C:13]([Cl:15])[C:12]([CH:16]([OH:25])[CH2:17][CH:18]2[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]2)=[C:11]([Cl:26])[N:10]=1>CS(C)=O>[NH2:8][C:9]1[N:10]=[C:11]([Cl:26])[C:12]([C:16](=[O:25])[CH2:17][CH:18]2[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]2)=[C:13]([Cl:15])[N:14]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 582011951-(2-Amino-4,6-dichloropyrimidin-5-yl)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethan-1-ol

Product 1

HCID 58201197HCID 58201197, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Triethylamine (5.25 mL) and a sulfur trioxide-pyridine complex (2.45 g) were added to a mixture composed of the above 1-(2-amino-4,6-dichloropyrimidin-5-yl)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethan-1-ol (2.32 g) and dimethyl sulfoxide (30 mL) under cooling in an ice bath. The ice bath was removed and the mixture was stirred for two hours. The reaction mixture was added dropwise to a 0.5 N hydrochloric acid solution (300 mL), followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and brine and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the solvent was evaporated to obtain a crude product of the title compound (2.08 g, 90%) as a solid. The resulting compound was directly used for the next reaction without purification.

Workup

  1. temperatureunder cooling in an ice bath
  2. customThe ice bath was removed
  3. additionThe reaction mixture was added dropwise to a 0.5 N hydrochloric acid solution (300 mL)
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was sequentially washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-145b240b2b4547cda25a0dc40d72b5b1
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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