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

HRID 2116449Notes

Reaction equation

HRID 2116449 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

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 222689244,6-Dichloro-5-nitro-2-(propylthio)pyrimidine

Product 1

HCID 859081644-[6-Chloro-5-nitro-2-(propylthio)pyrimidin-4-yl]morpholine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

Workup

  1. customAfter 1 h the solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialthe organics dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 25% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-2992591711a44dad83bc7fe3ce61f69d
Source dataset
uspto-grants-2008_10
Patent number
US07439240B2

Reaction notes

Loading…