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Sodium hydride → HCID 11202706, Verbindung

HRID 2377877
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2377877
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:18]1[N:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[C:19]=1[N+:35]([O-:37])=[O:36]>CN(C)C(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:18]2[C:19]([N+:35]([O-:37])=[O:36])=[C:20]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:29][CH:30]=3)[N:21]=[CH:22][N:23]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 218978866-Chloro-N-(4-(methylsulfonyl)phenyl)-5-nitropyrimidin-4-amine

Produkt 1

HCID 11202706HCID 11202706, VerbindungAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374Dimethylacetamide
Lösungsmittel

Versuchsvorschrift

3-Hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.65 mmol, 131 mg) and sodium hydride (1.3 mmol, 31 mg) were dissolved in N,N-dimethyl acetamide (1.5 mL) and stirred for 30 minutes at room temperature. Then, (6-chloro-5-nitro-pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)-amine (0.26 mmol, 84 mg) was added. The reaction was stirred at 70° C. for 30 minutes. Its progress was monitored by thin layer chromatography and LCMS. Sodium hydride was quenched with water and the desired compound was extracted in ethyl acetate. Organic solvents were evaporated in vacuo. Flash chromatography (Silica gel 60; 50/50 EtoAc/Hexanes) provided Compound A16 as a yellow solid (96 mg, 54%). 1H NMR (400 MHz, CDCl3) δ (ppm): 10.21 (s, 1H), 8.41 (s, 1H), 7.97 (d, 2H), 7.86 (d, 2H), 4.52 (m, 2H), 3.49 (m, 2H), 3.11 (s, 3H), 2.75 (m, 1H), 1.84 (m, 2H), 1.65 (m, 2H), 1.46 (s, 9H). LCMS (ESI), m/z 394.1 (M+H+, 100%).

Aufarbeitung

  1. stirringThe reaction was stirred at 70° C. for 30 minutes
  2. customSodium hydride was quenched with water
  3. extractionthe desired compound was extracted in ethyl acetate
  4. customOrganic solvents were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c0ad252841c14531aecf4263cc9d0ca1
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07470699B2

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