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Tetrabutylammonium Fluoride → (2S)-ethyl 2-(2-amino-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

HRID 1468749
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HRID 1468749 반응식
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:43])=[N:14][C:15]2[N:16]([N:30]=[C:31]([NH:33]C(OCC[Si](C)(C)C)=O)[CH:32]=2)[C:17]=1[C:18]1[C:19]([CH3:29])=[C:20]2[C:25](=[C:26]([F:28])[CH:27]=1)[O:24][CH2:23][CH2:22][CH2:21]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:33][C:31]1[CH:32]=[C:15]2[N:14]=[C:13]([CH3:43])[C:12]([C@H:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:17]([C:18]3[C:19]([CH3:29])=[C:20]4[C:25](=[C:26]([F:28])[CH:27]=3)[O:24][CH2:23][CH2:22][CH2:21]4)[N:16]2[N:30]=1
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참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86695369(2S)-ethyl 2-tert-butoxy-2-(7-(8-fluoro-5-methylchroman-6-yl)-5-methyl-2-((2-(trimethylsilyl)ethoxy)carbonylamino)pyrazolo[1,5-a]pyrimidin-6-yl)acetate

생성물 1

HCID 86695370(2S)-ethyl 2-(2-amino-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate수율 85.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

A mixture of (2S)-ethyl 2-tert-butoxy-2-(7-(8-fluoro-5-methylchroman-6-yl)-5-methyl-2-((2-(trimethylsilyl)ethoxy)carbonylamino)pyrazolo[1,5-a]pyrimidin-6-yl)acetate (2.3 g, 3.74 mmol), 1M TBAF (4.49 mL, 4.49 mmol) in THF (20 mL) was stirred at rt for 3 h. It was then concentrated, diluted with water, and extracted with EtOAc. The organic phase was washed with water, dried over MgSO4, filtered and concentrated to yield 1.5 g (85%) of (2S)-ethyl 2-(2-amino-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate as a oil which solidified upon standing for one day. 1H NMR (500 MHz, CDCl3) δ 6.87 (d, J=10.56 Hz, 1H), 5.88 (s, 1H), 4.85 (s, 1H), 4.33 (t, J=5.04 Hz, 2H), 4.08-4.14 (m, 4H), 2.76 (t, J=6.38 Hz, 2H), 2.71 (s, 3H), 2.13-2.21 (m, 2H), 1.87 (s, 3H), 1.20 (t, J=7.17 Hz, 3H), 1.16 (s, 9H). LCMS (M+H)=471.36.

후처리

  1. concentrationIt was then concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-444bc25021b940d7b076c1fc5d7e1528
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09006235B2

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