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Methanesulfonic Acid → 7,8-dihydro-1,3-dimethyl-1H-imdazo[1,2-c]pyrazolo[3,4-e]pyrimidine

HRID 2417656
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2417656
[CH3:1][N:2]1[C:6]([C:7]2[NH:8][CH2:9][CH2:10][N:11]=2)=[C:5]([N+:12]([O-])=O)[C:4]([CH3:15])=[N:3]1.[CH2:16](OC(OCC)OCC)C.CS(O)(=O)=O>C(O)C>[CH3:1][N:2]1[C:6]2[C:7]3[N:8]([CH2:9][CH2:10][N:11]=3)[CH:16]=[N:12][C:5]=2[C:4]([CH3:15])=[N:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6395Methanesulfonic AcidHCID 31214Ethyl orthoformateHCID 133383765-(4,5-Dihydro-1H-imidazol-2-yl)-1,3-dimethyl-4-nitro-1H-pyrazole

Produkt 1

HCID 133383787,8-dihydro-1,3-dimethyl-1H-imdazo[1,2-c]pyrazolo[3,4-e]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The above nitro compound (8.4 g, 0.04 mol) is dissolved in 150 ml of methanol and hydrogenated (initial hydrogen pressure=51 psi) in the presence of 0.5 g of Raney nickel until the theoretical uptake of hydrogen is observed. The catalyst is removed by filtering; the filtrate is evaporated in vacuo to give 7.4 g (0.04 mol) of a purple oil (characterized by its IR-spectrum) of 2-(4-amino-1,3-dimethyl-5-pyrazolyl)imidazoline. This amine (7.4 g, 0.04 mol) is stirred under reflux 1.5 hr in a mixture of 20 ml absolute ethanol, 50 ml of triethylorthoformate and 1 ml of methanesulfonic acid. The mixture is evaporated in vacuo. The product is dissolved in methylenedichloride (100 ml) and washed with 100 ml of dilute ammonium hydroxide; the organic layer is dried over MgSO4 and evaporated in vacuo to give 7,8-dihydro-1,3-dimethyl-1H-imdazo[1,2-c]pyrazolo[3,4-e]pyrimidine 1.5 hydrate, mp 80°-82° C. from ethyl acetate-pet ether.

Aufarbeitung

  1. customThe mixture is evaporated in vacuo
  2. dissolutionThe product is dissolved in methylenedichloride (100 ml)
  3. washwashed with 100 ml of dilute ammonium hydroxide
  4. dry with materialthe organic layer is dried over MgSO4
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fac3b4cec5fd4c2185717c44b9cc5da3
Quelldatensatz
uspto-grants-1984_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04469868

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