Triethylamine → HCID 12163139, Verbindung

HRID 511558

Reaktionsgleichung

Reaktionsgleichung von HRID 511558
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.[CH3:16][NH:17][CH2:18][C:19]#[CH:20].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[Cl:11][C:6]1[C:7]([C:8]([N:17]([CH3:16])[CH2:18][C:19]#[CH:20])=[O:10])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 96160N-methylpropyn-2-ylamineHCID 248204874,6-Dichloropyrimidine-5-carboxylic acid2×

Produkt 1

HCID 12163139HCID 12163139, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4,6-dichloropyrimidine-5-carboxylic acid (Compound 310G, 15.0 g, 77.7 mmol) and thionyl chloride (28.3 mL, 389 mmol) was refluxed in DCM (100 mL) for 2 h. The reaction mixture was concentrated in vacuo, taken up in DMF (200 mL) and charged drop-wise with a solution of N-methyl-2-propyn-1-amine (5.4 g, 78 mmol) and triethylamine (21.7 mL, 155 mmol) in DMF at −60° C. and stirred at rt for 24 h. The reaction mixture was partitioned between EtOAc and water and separated. The aqueous layer was extracted with EtOAc (3×) and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated. The compound was purified on an Isco Combiflash to afford 7.66 g, 40% yield, of the title compound. 1H NMR (DMSO-d6, 400 MHz): δ=9.04 (s, 1H), 4.37 (d, J=2.53 Hz, 2H), 3.08 (s, 1H), 2.95 (s, 3H). MS (ES+): m/z 246.0039 [MH+] (TOF, polar).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. customseparated
  4. extractionThe aqueous layer was extracted with EtOAc (3×)
  5. washthe combined organic fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe compound was purified on an Isco Combiflash
  10. customto afford 7.66 g, 40% yield

Quellen und Nachweise

ORD-Eintrag
ord-743ba29af3f5416b9ebd4809c8e6ff50
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096624B2

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