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Sodium hydride → (S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methyl-2-(((5-methyl-2-((S)-pent-4-en-2-yloxy)benzyl)oxy)methyl)pyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

HRID 921137
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Reaktionsgleichung

Reaktionsgleichung von HRID 921137
[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH2:20]I)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:22])[C:12]=2[C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[CH3:35][C:36]1[CH:37]=[CH:38][C:39]([O:44][C@H:45]([CH2:47][CH:48]=[CH2:49])[CH3:46])=[C:40]([CH2:42][OH:43])[CH:41]=1.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH2:20][O:43][CH2:42][C:40]4[CH:41]=[C:36]([CH3:35])[CH:37]=[CH:38][C:39]=4[O:44][C@H:45]([CH2:47][CH:48]=[CH2:49])[CH3:46])[CH:19]=[C:15]3[N:14]=[C:13]([CH3:22])[C:12]=2[C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 118307102(S)-(5-methyl-2-(pent-4-en-2-yloxy)phenyl)methanolHCID 118318796(S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(iodomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Produkt 1

HCID 131734906(S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methyl-2-(((5-methyl-2-((S)-pent-4-en-2-yloxy)benzyl)oxy)methyl)pyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate
Ausbeute 22,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

(S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(iodomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.45 g, 0.770 mmol) was dissolved in 1 mL DMF to this was added (S)-(5-methyl-2-(pent-4-en-2-yloxy)phenyl)methanol (0.191 g, 0.924 mmol) as a solution in 1 mL DMF. NaH-60% wt/wt in oil (47 mg, 1.16 mmol) was added and the reaction mixture was stirred for 5 hours. The reaction was quenched with 1N HCl then transferred to a separatory funnel where the product was extracted with ethyl acetate. The organic solution was dried over Na2SO4. After filtration the solvent was removed under vacuum and the product purified by silica gel chromatography using a Biotage apparatus to isolate the title compound as an oil (114 mg). 1H NMR (400 MHz, CDCl3) δ 1.21-1.24 (15H, overlapping s and m), 1.32 (3H, d), 1.65-1.8 (4H, br m), 2.35 (3H, s), 2.50 (2H, m), 2.61 (3H, s), 3.0-3.5 (4H, very broad m), 3.75 (2H, s), 4.21 (2H, m), 4.45 (1H, m), 4.66 (2H, br s), 4.77 (2H, s), 5.06-5.22 (4H, overlapping m), 5.32 (1H, s), 5.85-6.2 (2H, overlapping m), 6.59 (1H, s), 6.71 (1H, s), 6.77 (1H, d), 7.34 (1H, d).

Aufarbeitung

  1. customThe reaction was quenched with 1N HCl
  2. customthen transferred to a separatory funnel
  3. extractionwhere the product was extracted with ethyl acetate
  4. dry with materialThe organic solution was dried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under vacuum
  7. customthe product purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9dff74479d8d4300952c5d39b1994a49
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09273067B2

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