Cesium fluoride → N-Cyclopropyl-4-methyl-3-(2-(2-morpholinoethyl)thieno[2,3-d]pyrimidin-6-yl)benzamide

HRID 19573노트

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HRID 19573 반응식
Br[C:2]1[S:18][C:5]2[N:6]=[C:7]([CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:8]=[CH:9][C:4]=2[CH:3]=1.[CH:19]1([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:21][CH2:20]1.[F-].[Cs+].O1CCOCC1>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH:19]1([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([C:2]3[S:18][C:5]4[N:6]=[C:7]([CH2:10][CH2:11][N:12]5[CH2:17][CH2:16][O:15][CH2:14][CH2:13]5)[N:8]=[CH:9][C:4]=4[CH:3]=3)[CH:25]=2)[CH2:20][CH2:21]1

참가 물질

8

반응물 4

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 685604506-Bromo-2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine

생성물 1

HCID 68562325N-Cyclopropyl-4-methyl-3-(2-(2-morpholinoethyl)thieno[2,3-d]pyrimidin-6-yl)benzamide

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

A 5 ml glass microwave reaction vessel was charged with 6-bromo-2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine. (0.200 g, 0.582 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.135 g, 0.582 mmol), cesium fluoride (0.277 g, 1.75 mmol), tetrakis(triphenylphosphine)palladium(0) (0.046 g, 0.040 mmol), 1,4-dioxane (1 mL, 57 mmol) and water (1 ml). The reaction mixture was heated in a Smith Synthesizer microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 150° C. for 20 min. The reaction mixture was diluted with EtOAc and filtered through Celite®. The organic solutions were evaporated under reduced pressure. The crude residue was suspended in DCM and washed with saturated sodium bicarbonate (1×25 mL) followed by brine (1×25 mL), water (1×25 mL) and dried over MgSO4. The organic solutions were evaporated under reduced pressure and the residue 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 (0.095 g) MS (ES+): 438 (M+H)+.

후처리

  1. filtrationfiltered through Celite®
  2. customThe organic solutions were evaporated under reduced pressure
  3. washwashed with saturated sodium bicarbonate (1×25 mL)
  4. dry with materialdried over MgSO4
  5. customThe organic solutions were evaporated under reduced pressure
  6. customchromatographed through a Redi-Sep pre-packed silica gel column (40 g)
  7. washeluting with a gradient of 5% to 95% MeOH in DCM

출처 및 근거

ORD 기록
ord-e9bbad521c00484a8ff2f111f19a385b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745449B2

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