Water → (7S)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7H-pteridin-6-one

HRID 2364757Notes

Reaction equation

HRID 2364757 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C@H:6]([CH2:13][CH3:14])[N:5]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:4]=2[N:3]=1.[C:20]1(C)C=CC(S(OC)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:20])[C:7](=[O:12])[C@H:6]([CH2:13][CH3:14])[N:5]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 86668256(7S)-2-chloro-8-cyclopentyl-7-ethyl-5,7-dihydropteridin-6-one

Product 1

HCID 86668257(7S)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7H-pteridin-6-oneYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(7S)-2-Chloro-8-cyclopentyl-7-ethyl-5,7-dihydropteridin-6-one 41e (2.80 g, 10 mmol) was dissolved in 50 mL of acetone followed by the addition of methyl p-toluenesulfonate (2.80 g, 15 mmol) and potassium carbonate (2.76 g, 20 mmol) successively, stirred for 12 hours. The resulting solution was added with 50 mL of water and extracted with ethyl acetate (100 mL×3). The combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure, The resulting residue was purified by silica gel column chromatography with elution system B to obtain the title compound (7S)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7H-pteridin-6-one 41f (2.50 g, yield: 85.0%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (100 mL×3)
  2. washThe combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-f026b4c79c0a497e9a78e0a8a9591c4c
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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