Trimethylsulfonium iodide → 7-(1-oxaspiro[2.5]oct-6-yl)-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 51609

반응식

HRID 51609 반응식
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]3[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[I-].[CH3:32][S+](C)C.CC(C)([O-])C.[K+]>O1CCCC1.CS(C)=O>[O:30]1[C:27]2([CH2:26][CH2:25][CH:24]([N:8]3[C:4]4[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=4[C:10]([C:11]4[CH:12]=[CH:13][C:14]([O:17][C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)=[CH:15][CH:16]=4)=[CH:9]3)[CH2:29][CH2:28]2)[CH2:32]1

참가 물질

6

반응물 3

HCID 75127Trimethylsulfonium iodideHCID 22736171Protein kinase inhibitor 9HCID 23665647Potassium tert-butoxide

생성물 1

HCID 227362447-(1-oxaspiro[2.5]oct-6-yl)-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine수율 92%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-5 °C

실험 절차

To a mixture of 4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-cyclohexanone (2 g, 5 mmol) in tetrahydrofuran (17.5 mL) were added trimethyl-sulfonium iodide (1.53 g, 7.5 mmol) in dimethyl sulfoxide (25 mL) and potassium-t-butoxide (7.5 mL, 7.5 mmol, 1 M in tetrahydrofuran) under an atmosphere of nitrogen at −5° C. The mixture was stirred at −5° C. for 1 hour. The mixture was poured into ice water (50 mL). The water phase was extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with saturated ammonium chloride solution (2×30 mL), water (1×30 mL), and brine (2×30 mL) and dried over sodium sulfate. The solvent was removed under reduced pressure to yield 7-(1-oxaspiro[2.5]oct-6-yl)-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (1.9 g, 4.6 mmol, 2:1-mixture of trans and cis). The mixture was suspended in dichloromethane (3 mL). The solid was filtered and was washed with dichloromethane (1 mL) to yield 7-(1-oxaspiro[2.5]oct-6-yl)-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.994 g, 2.4 mmol, 4:1-mixture of trans and cis).

후처리

  1. extractionThe water phase was extracted with ethyl acetate (3×30 mL)
  2. washThe combined organic extracts were washed with saturated ammonium chloride solution (2×30 mL), water (1×30 mL), and brine (2×30 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-74cb1f5765634d9b8ee9282b0a042ec9
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713474B2

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