3-Ethoxy-1,2-propanediol → HCID 15346469, compound

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

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).