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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
ノート
印刷プレビュー

反応式

HRID 1468749 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 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)acetate収率 85.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-444bc25021b940d7b076c1fc5d7e1528
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09006235B2

反応ノート

読み込み中…

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