3-Ethoxypropane-1,2-diol → HCID 15346469, compound

HRID 342477Notes

Reaction equation

HRID 342477 reaction equation
[CH2:1]1[O:20][C:4]2([CH2:9][CH2:8][CH:7]([NH:10][C:11]3[C:16]([Cl:17])=[C:15]([CH2:18][CH3:19])[N:14]=[CH:13][N:12]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[CH2:21]([O:23][CH2:24]C(O)CO)[CH3:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:17][C:16]1[C:11]([NH:10][CH:7]2[CH2:6][CH2:5][C:4]3([O:20][CH:1]([CH2:24][O:23][CH2:21][CH3:22])[CH2:2][O:3]3)[CH2:9][CH2:8]2)=[N:12][CH:13]=[N:14][C:15]=1[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 942153-Ethoxypropane-1,2-diolHCID 521998p-Toluenesulfonic acid monohydrateHCID 57130834HCID 57130834, compound

Product 1

HCID 15346469HCID 15346469, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.0 g (10 mmol) of 4-(5-chloro-6-ethylpyrimidin-4-ylamino)-cyclohexanone ethylene ketal and 10 ml of 3-ethoxypropane-1,2-diol together with 100 mg of p-toluenesulfonic acid hydrate were refluxed for 8 hours in 10 ml of toluene. The reaction mixture was extracted by stirring with dilute sodium hydroxide solution and water, the organic phase was dried, and the solvent was stripped off in vacuo. The crude product was purified by silica gel chromatography (eluent petroleum ether/ethyl acetate 3:2). This gave 2.0 g (56.3% of theory) of a colorless oil (diastereomer mixture).

Workup

  1. extractionThe reaction mixture was extracted
  2. customthe organic phase was dried
  3. customThe crude product was purified by silica gel chromatography (eluent petroleum ether/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-889fcfdc3a70499389d8e1964c3b178c
Source dataset
uspto-grants-1999_01
Patent number
US05859009

Reaction notes

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