Hydrochloric Acid → 4-t-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyl]benzenesulfonamide

HRID 1418330Notes

Reaction equation

HRID 1418330 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([Cl:30])[N:18]=[C:17](Cl)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.O.Cl>CS(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([Cl:30])[N:18]=[C:17]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[N:16]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8083MorpholineHCID 867538724-t-butyl-N-[2,6-dichloro-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide

Product 1

HCID 227294144-t-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyl]benzenesulfonamideYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-t-Butyl-N-[2,6-dichloro-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide (5) (482 mg; 1.0 mmol) was dissolved in dimethyl sulfoxide (5 ml). Morpholine (175 mg; 2.0 mmol) was added to the solution, and the resultant mixture was stirred overnight at 100° C. After being cooled, the reaction mixture was poured into water, made acidic with hydrochloric acid, and extracted with ethyl acetate, being washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2), to thereby obtain 240 mg (yield: 45%) of the title compound as a white powder.

Workup

  1. temperatureAfter being cooled
  2. extractionextracted with ethyl acetate
  3. washbeing washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-ebe58f8e95514036b06e3790f3aab0ec
Source dataset
uspto-grants-1999_03
Patent number
US05883092

Reaction notes

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