4-[4-Chloro-5-(2-chloro-5-methoxy-phenoxy)-6-methyl-pyrimidin-2-yl]-morpholine → 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

HRID 37091

Reaction equation

HRID 37091 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[Cl:17])=[C:6]([CH3:18])[N:5]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1.[K].[C:26]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27]>CS(C)=O>[C:26]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH:39][C:2]2[C:7]([O:8][C:9]3[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=3[Cl:17])=[C:6]([CH3:18])[N:5]=[C:4]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:3]=2)(=[O:37])=[O:38])=[CH:32][CH:31]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 189389104-[4-Chloro-5-(2-chloro-5-methoxy-phenoxy)-6-methyl-pyrimidin-2-yl]-morpholineHCID 66748434p-t-Butylbenzenesulfonamide potassium

Product 1

HCID 199347354-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamideYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10.7 g of 4-[4-chloro-5-(2-chloro-5-methoxy-phenoxy)-6-methyl-pyrimidin-2-yl]-morpholine and 21.6g of p-t-butyl-benzene sulphonamide potassium in 150 ml of dry dimethyl sulphoxide were heated to 120° C. under argon for 16 hours. Thereafter, the dimethylsulphoxide was distilled off, the residue was partitioned between ethyl acetate and 1N hydrochloric acid and the organic phase was washed neutral. The organic phase was dried, the solvent was evaporated and the residue was recrystallized from dichloromethane-ethanol. There were obtained 14.7 g 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide, m.p 154° C., MS: M=546.

Workup

  1. distillationThereafter, the dimethylsulphoxide was distilled off
  2. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  3. washthe organic phase was washed neutral
  4. customThe organic phase was dried
  5. customthe solvent was evaporated
  6. customthe residue was recrystallized from dichloromethane-ethanol

Sources & evidence

ORD record
ord-dc856f450a234514a5ac03c174fae505
Source dataset
uspto-grants-1995_05
Patent number
US05420129

Linked notes

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