Acetonitrile → Tert-butyl 4-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate

HRID 624719

Reaktionsgleichung

Reaktionsgleichung von HRID 624719
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(N(CC)CC)C.C(#N)C>O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 58314523Tert-butyl 4-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the reaction flask, 5,7-dichloropyrazolo[1,5-a]pyrimidine (896 mg, 4.8 mmol) was added along with tert-butyl 4-aminopiperidine-1-carboxylate (954 mg, 4.8 mmol), triethylamine (664 μL, 4.8 mmol), and acetonitrile (16 mL). The reaction was heated at 100° C. for 12 hours then cooled to room temperature, diluted with water, filtered and washed with water. The product, tert-butyl 4-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate, was collected as a solid in quantitative yield and dried under vacuum overnight. LCMS (M+1=352)

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered
  3. washwashed with water
  4. customThe product, tert-butyl 4-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate, was collected as a solid in quantitative yield
  5. customdried under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-2617cc04c67b4e199341ad96ea4ed970
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303033B2

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