Sodium hydride → 2-Chloro-7,7-dimethyl-4-morpholin-4-yl-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([O:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[O:9][CH2:10][C:11]([CH3:14])([CH3:12])[O:13][C:6]=2[N:7]=1Participants
4
Procedure
To a solution of 1-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-2-methyl-propan-2-ol (2.18 g, 6.77 mmol) in THF (150 mL) was added sodium hydride (812 mg, 20.31 mmol, 60% dispersion in mineral oil) and the resulting mixture stirred at RT for 5 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The resultant residue was triturated with cyclohexane affording 2-Chloro-7,7-dimethyl-4-morpholin-4-yl-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine as a white solid (1.35 g, 70%). LCMS: RT=3.03 min, [M+H]+=286/288.