Tetrabutylammonium Fluoride → 2-(2-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-ol

HRID 2262294노트

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Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[CH:10]=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[S:8][C:6]=2[N:7]=1.[CH3:21][C:22]1[N:39](COCC[Si](C)(C)C)[C:25]2=[N:26][CH:27]=[C:28](C3OC(C)(C)C(C)(C)O3)[CH:29]=[C:24]2[N:23]=1.C[Si](C)(C)CCOCN1C2C=C(C3N=C(N4CCOCC4)C4C=C(C(O)(C)C)SC=4N=3)C=CC=2N=C1C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:21][C:22]1[NH:39][C:25]2=[N:26][CH:27]=[C:28]([C:2]3[N:3]=[C:4]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:5]4[CH:10]=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[S:8][C:6]=4[N:7]=3)[CH:29]=[C:24]2[N:23]=1

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2-(2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-ol (100 mg) was reacted with 161 mg of 3-((2-(trimethylsilyl)ethoxy)methyl)-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-imidazo[4,5-b]pyridine 54 via Example 6b and General Procedure A. Crude 2-(2-(1-((2-(trimethylsilyl)ethoxy)methyl)-2-methyl-1H-benzo[d]imidazol-6-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-ol was then refluxed overnight with 2 equivalents of tetrabutylammoniumfluoride in THF to remove the SEM protecting group. The crude material was then extracted with water and ethyl acetate. The organic layer was concentrated to dryness and then purified via reverse phase HPLC to give 5.1 mg of 414. MS (Q1) 411.2 (M)+

후처리

customto remove the SEM
extractionThe crude material was then extracted with water and ethyl acetate
concentrationThe organic layer was concentrated to dryness
custompurified via reverse phase HPLC

출처 및 근거

ORD 기록: ord-85f02f7878cf494abd8e1dc6be60046c
출처 데이터셋: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07846929B2

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