Methanol → HCID 53685887, compound

HRID 2287369Notes

Reaction equation

HRID 2287369 reaction equation
[Na].Cl[C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH:15][S:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:18])=[O:17])[C:4]=1[O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([O:36][CH3:37])=[O:35])=[CH:30][C:29]=1[CH2:38][CH2:39][CH3:40].[CH3:41][OH:42]>Cl>[CH3:41][O:42][C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH:15][S:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:18])=[O:17])[C:4]=1[O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([O:36][CH3:37])=[O:35])=[CH:30][C:29]=1[CH2:38][CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 54411816HCID 54411816, compound

Product 1

HCID 53685887HCID 53685887, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Sodium (356 mg) was dissolved in 20 ml of methanol and 900 mg of N-[6-chloro-5-(4-methoxycarbonyl-2-propylphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide was added thereto with stirring at room temperature. The reaction mixture was stirred at room temperature for five hours and forty minutes, at 60° C. for one hour and fifty minutes and at room temperature overnight. After that, the mixture was poured into a mixture of IN hydrochloric acid and ice. Crystals separated out therefrom were collected by filtration and the resulting crystals were purified by a silica gel column chromatography (chloroform-ethanol=20:1). The resulting amorphous substance was crystallized in ether and collected by filtration to give 452 mg of N-[6-methoxy-5-(4-methoxycarbonyl-2-propylphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for five hours and forty minutes, at 60° C. for one hour and fifty minutes and at room temperature overnight
  2. customCrystals separated out
  3. filtrationtherefrom were collected by filtration
  4. customthe resulting crystals were purified by a silica gel column chromatography (chloroform-ethanol=20:1)
  5. customThe resulting amorphous substance was crystallized in ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-51425a934043432a807d5a3fc1d8ec7d
Source dataset
uspto-grants-2000_07
Patent number
US06083955

Reaction notes

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