Diisopropylethylamine → HCID 86649284, Verbindung

HRID 450390

Reaktionsgleichung

Reaktionsgleichung von HRID 450390
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4](Cl)[N:3]=1.[CH3:13][C:14]1[NH:18][N:17]=[C:16]([NH2:19])[CH:15]=1.CC[N:22](C(C)C)C(C)C.N[C:30]1[CH:35]=[CH:34][O:33][CH2:32][CH:31]=1>CCO.O.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:19]([C:16]2[CH:15]=[C:14]([CH3:13])[NH:18][N:17]=2)[CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:22])[N:3]=1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 42978432,4,6-Trichloro-5-nitropyrimidine2×HCID 17791271HCID 17791271, Verbindung

Produkt 1

HCID 86649284HCID 86649284, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2,4,6-trichloro-5-nitro pyrimidine (Intermediate 37, 1 g, 4.4 mmol) in EtOH at −50° C. were added 5-methyl-1H-pyrazol-3-amine (255 mg) and DIPEA (1.6 ml) drop-wise. The resulting mixture was stirred at this temperature for 5 minutes whereupon 4-amino pyran (300 mg) was added. The resulting mixture was allowed to warm to ambient temperature for 4 hours. The mixture was diluted with H2O and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, saturated NaHCO3 (aq) solution, dried and evaporation of the volatiles under reduced pressure gave a colored residue. Purification by Gilson (MeCN/H2O, 5%→95%, 15 minutes) gave the title compound (120 mg). LCMS: 354 [M+1].

Aufarbeitung

  1. additionwas added
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine, saturated NaHCO3 (aq) solution
  4. customdried
  5. customevaporation of the volatiles under reduced pressure
  6. customgave a colored residue
  7. customPurification by Gilson (MeCN/H2O, 5%→95%, 15 minutes)

Quellen und Nachweise

ORD-Eintrag
ord-0cac8eba3950473ca5dbaaedd86949aa
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486966B2

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