Ethyl Acetate → 4-t-butyl-N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyl]-benzenesulfonamide

HRID 1418331Notes

Reaction equation

HRID 1418331 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[H-].[Na+].[C:8]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:22]2[C:27]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])=[C:26](Cl)[N:25]=[C:24]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)[N:23]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].C(OCC)(=O)C>CS(C)=O>[C:8]([C:12]1[CH:13]=[CH:14][C:15]([S:18]([NH:21][C:22]2[C:27]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])=[C:26]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[N:25]=[C:24]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)[N:23]=2)(=[O:20])=[O:19])=[CH:16][CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 227294144-t-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyl]benzenesulfonamide

Product 1

HCID 153811024-t-butyl-N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyl]-benzenesulfonamideYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,3-Propanediol (580 mg) was dissolved in dimethyl sulfoxide (15 ml). Sodium hydride (297 mg) and 4-t-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyl]benzenesulfonamide (1.1 g) were added to the solution. The resultant mixture was stirred for 4 hours at 120° C. Ethyl acetate was added to the reaction mixture, followed by successive washing with 0.5N-HCl, water, and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1), to thereby obtain 802 mg (yield: 68%) of the title compound as a white powder.

Workup

  1. washby successive washing with 0.5N-HCl, water, and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-7352672f72594bb5944891d3fb9b61ce
Source dataset
uspto-grants-1999_03
Patent number
US05883092

Reaction notes

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