Morpholine → 2-(Methylsulfonyl)-4-(5-(morpholinosulfonyl)thiophen-2-yl)pyrimidine

HRID 507550

반응식

HRID 507550 반응식
CS[C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([S:14](Cl)(=[O:16])=[O:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[CH2:24](N(CC)CC)C.OO[S:33]([O-:35])=[O:34].[K+]>O1CCCC1.CC(C)=O.O.O>[CH3:24][S:33]([C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([S:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)(=[O:16])=[O:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1)(=[O:35])=[O:34]

참가 물질

8

반응물 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 27369955-(2-(Methylthio)-4-pyrimidinyl)-2-thiophenesulfonyl chlorideHCID 23707502Potassium hydroxy sulfite

생성물 1

HCID 602043782-(Methylsulfonyl)-4-(5-(morpholinosulfonyl)thiophen-2-yl)pyrimidine수율 73.5%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 18366337Propan-2-one--water (1/1)용매

실험 절차

A mixture of 5-(2-(methylthio)pyrimidin-4-yl)thiophene-2-sulfonyl chloride (200 mg, 0.65 mmol), morpholine (62 mg, 0.72 mmol) and triethylamine (78 mg, 0.78 mmol) in tetrahydrofuran (5 mL) was stirred at rt for 2 days. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo and the residue was washed with diethyl ether (2 mL) to give a white solid. The solid was dissolved in 30 mL of acetone-water (1:1) and then oxone (2 g) was added. After stirring at rt for 20 h the mixture was concentrated in vacuo to remove the acetone. The white precipitate was filtered off, washed with water and dried to afford the title compound (186 mg, 73%). MS (M+H)+ 390.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layer was washed with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated in vacuo
  6. washthe residue was washed with diethyl ether (2 mL)
  7. customto give a white solid
  8. stirringAfter stirring at rt for 20 h the mixture
  9. concentrationwas concentrated in vacuo
  10. customto remove the acetone
  11. filtrationThe white precipitate was filtered off
  12. washwashed with water
  13. customdried

출처 및 근거

ORD 기록
ord-8690195d7efc4f38b511169274fd3a82
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

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