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Triethylamine → 4-(1-(but-3-enyl)hydrazinyl)-2-chloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide

HRID 2357979
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2357979
[CH2:1]([NH:5][NH2:6])[CH2:2][CH:3]=[CH2:4].[Cl:7][C:8]1[N:13]=[C:12](Cl)[C:11]([C:15]([NH:17][C:18]2[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:25])=[O:16])=[CH:10][N:9]=1.C(N(CC)CC)C>C1COCC1>[CH2:1]([N:5]([C:12]1[C:11]([C:15]([NH:17][C:18]2[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:25])=[O:16])=[CH:10][N:9]=[C:8]([Cl:7])[N:13]=1)[NH2:6])[CH2:2][CH:3]=[CH2:4]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 20337519HCID 20337519, VerbindungHCID 588368852,4-Dichloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide

Produkt 1

HCID 588368794-(1-(but-3-enyl)hydrazinyl)-2-chloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1.3 g (14.9 mmol) of 3-butenylhydrazine in 60 mL of THF was cooled to 0° C. and treated sequentially with 4.0 g (13.5 mmol) of 2,4-dichloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide 30 (Example 1, Step B) and 2.1 mL (14.9 mmol) of triethylamine. The resulting yellow slurry was warmed to room temperature and stirred for 23 h. The reaction mixture was quenched with saturated aqueous ammonium chloride (75 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 17:3) to give the title compound. 1H-NMR (DMSO-d6) δ 2.24 (s, 6H), 2.40-2.48 (m, 2H), 3.32 (s, 2H), 3.80 (t, J=7.3 Hz, 2H), 5.03 (dd, J=10.3 Hz, 1.1 Hz, 1H), 5.13 (dd, J=17.2 Hz, 1.5 Hz, 1H), 5.75-5.86 (m, 1H), 7.07 (s, 3H), 8.15 (s, 1H), 9.61 (s, 1H). Mass Spectrum (ESI) m/e=346.1 (M+1).

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (75 mL)
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 17:3)

Quellen und Nachweise

ORD-Eintrag
ord-d8cdd796d50b420c84dbe63cee48bf16
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07763624B2

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