Selenium Dioxide → 5-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-morpholin-4-yl-pyrimidin-4-ylamide

HRID 356652Notes

Reaction equation

HRID 356652 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:3]=1[O:4][C:5]1[C:6]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=2)(=[O:21])=[O:20])=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:9][C:10]=1[CH3:11].[Se](=O)=[O:38]>O1CCOCC1>[Cl:1][C:2]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:3]=1[O:4][C:5]1[C:6]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=2)(=[O:21])=[O:20])=[N:7][C:8]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[N:9][C:10]=1[CH:11]=[O:38]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 223778355-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-morpholin-4-yl-pyrimidin-4-ylamide

Product 1

HCID 223778605-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-morpholin-4-yl-pyrimidin-4-ylamideYield 51.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1 g of the compound obtained in Example 36 and 2.1 g of selenium dioxide in 40 ml of dioxan were stirred in an autoclave at 170° C. for 7 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was dried, the solvent was evaporated and the residue was purified over silica gel with ethyl acetate/hexane. 0.53 g of 5-isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-morpholin-4-yl-pyrimidin-4-ylamide, m.p. 194° C., was obtained.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic phase was dried
  5. customthe solvent was evaporated
  6. customthe residue was purified over silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-c3b639ff2c404d589f278cae338f982e
Source dataset
uspto-grants-1998_11
Patent number
US05837708

Reaction notes

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