Morpholine → 4-[6-Chloro-5-nitro-2-(propylthio)pyrimidin-4-yl]morpholine

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12](Cl)[N:11]=[C:10]([S:18][CH2:19][CH2:20][CH3:21])[N:9]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:7][C:8]1[N:9]=[C:10]([S:18][CH2:19][CH2:20][CH3:21])[N:11]=[C:12]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[C:13]=1[N+:14]([O-:16])=[O:15]

Participants

Procedure

Morpholine (2.6 g) was added dropwise to a stirred solution of 4,6-dichloro-5-nitro-2-propylthiopyrimidine (8 g) and N,N-diisopropylethylamine (3.85 g) in acetonitrile (70 ml ) at 0° C. After 1 h the solvent was evaporated and the residue partitioned between ethyl acetate and water, the organics dried (MgSO4) and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 25% ethyl acetate in isohexane. Yield 7.1 g