4-[4-Chloro-5-(2-chloro-5-methoxy-phenoxy)-6-methyl-pyrimidin-2-yl]-morpholine → 5-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-morpholin-4-yl-pyrimidin-4-ylamide

HRID 356651Notes

Reaction equation

HRID 356651 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].[CH:26]([C:29]1[CH:30]=[CH:31][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[N:33][CH:34]=1)([CH3:28])[CH3:27]>CS(C)=O>[Cl:17][C:10]1[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:9]=1[O:8][C:7]1[C:2]([NH:38][S:35]([C:32]2[CH:31]=[CH:30][C:29]([CH:26]([CH3:28])[CH3:27])=[CH:34][N:33]=2)(=[O:37])=[O:36])=[N:3][C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[N:5][C:6]=1[CH3:18]

Participants

4

Reactant 2

HCID 189389104-[4-Chloro-5-(2-chloro-5-methoxy-phenoxy)-6-methyl-pyrimidin-2-yl]-morpholineHCID 69289451179400-19-2

Product 1

HCID 223778355-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-morpholin-4-yl-pyrimidin-4-ylamideYield 77.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

9.2 g of 4-[4-chloro-5-(2-chloro-5-methoxy-phenoxy )-6-methyl-pyrimidin-2-yl]-morpholine and 17.8 g of 5-isopropyl-pyridine-2-sulphonamide potassium in 130 ml of dry dimethyl sulphoxide were heated to 120° C. under argon for 16 hours. Thereafter, the dimethyl sulphoxide was distilled off, the residue was partitioned between ethyl acetate and 1 N hydrochloric acid and the organic phase was washed neutral. The organic phase was dried, the solvent was evaporated and the residue was recrystallized from ethanol. 10.3 g of 5-isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy )-6-methyl-2-morpholin-4-yl-pyrimidin-4-ylamide, MS: M =534, were obtained.

Workup

  1. distillationThereafter, the dimethyl sulphoxide was distilled off
  2. customthe residue was partitioned between ethyl acetate and 1 N 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 ethanol

Sources & evidence

ORD record
ord-ae126cd29bc04115a85e40f0d17bf292
Source dataset
uspto-grants-1998_11
Patent number
US05837708

Reaction notes

Loading…