N-methyl-2-pyrrolidone → 2-(2-Morpholinoethyl)thieno[2,3-d]pyrimidine

HRID 19571

반응식

HRID 19571 반응식
CS([C:5]1[N:6]=[CH:7][C:8]2[CH:13]=[CH:12][S:11][C:9]=2[N:10]=1)(=O)=O.N[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.CN1CCCC1=O>CCOC(C)=O.O>[O:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][C:5]2[N:6]=[CH:7][C:8]3[CH:13]=[CH:12][S:11][C:9]=3[N:10]=2)[CH2:18][CH2:19]1

참가 물질

6

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 4082852-MorpholinoethylamineHCID 219883562-(Methylsulfonyl)thieno[2,3-d]pyrimidine

생성물 1

HCID 685591422-(2-Morpholinoethyl)thieno[2,3-d]pyrimidine수율 87.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-(methylsulfonyl)thieno[2,3-d]pyrimidine (1.0 g, 4.67 mmol), 4-(2-aminoethyl)morpholine (1.8 g, 14.02 mmol), and 1-methyl-2-pyrrolidinone (1.5 mL) was heated to 100° C. overnight. The reaction mixture was cooled to RT and diluted with EtOAc (200 mL)/water (75 mL). The layers were separated, and the organic layer was washed successively with water (4×75 mL) and brine (1×75 mL). The organic layer was then dried over MgSO4, filtered and concentrated to give (1.2 g) of the crude product. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 5% to 95% MeOH in DCM to provide the title compound (1.02 g) MS (ES+): 265 (M+H)+.

후처리

  1. customThe layers were separated
  2. washthe organic layer was washed successively with water (4×75 mL) and brine (1×75 mL)
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give (1.2 g) of the crude product
  7. customchromatographed through a Redi-Sep pre-packed silica gel column (40 g)
  8. washeluting with a gradient of 5% to 95% MeOH in DCM

출처 및 근거

ORD 기록
ord-d2b26d6d89424ae8a6597c6c0ad4a804
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745449B2

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