Dimethylformamide → methyl 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate

HRID 1853051

Reaktionsgleichung

Reaktionsgleichung von HRID 1853051
Cl.[NH:2]1[CH:6]=[C:5]([C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[N:8]=2)[CH:4]=[N:3]1.[CH:20]1([CH:23]=[CH:24][C:25]#[N:26])[CH2:22][CH2:21]1.CN(C=O)C.C1CCN2C(=NCCC2)CC1>CCOC(C)=O>[C:25]([CH2:24][CH:23]([N:2]1[CH:6]=[C:5]([C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[N:8]=2)[CH:4]=[N:3]1)[CH:20]1[CH2:22][CH2:21]1)#[N:26]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 670567823-CyclopropylacrylonitrileHCID 86685326methyl 5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate hydrochloride

Produkt 1

HCID 67456699methyl 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylateAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 100 mL flask, methyl 5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate hydrochloride (0.300 g, 1.07 mmol) and 3-cyclopropylacrylonitrile (Preparation B; 0.300 g, 3.22 mmol) were suspended in DMF (5.36 mL, 1.07 mmol) and DBU (0.722 mL, 4.83 mmol) added in one portion. The reaction mixture was stirred at ambient temperature for 15 hours. The reaction mixture was diluted in EtOAc and washed with water and brine. The combined organic layers were dried over MgSO4, filtered, and concentrated down to a yellow oil. Purification of the crude material by silica chromatography using a gradient of 50-100% EtOAc afforded methyl 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate (0.127 g, 0.378 mmol, 35.2% yield) as a yellow oil. MS (apci) m/z=337.2 (M+H).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated down to a yellow oil
  5. customPurification of the crude material by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e59a4f1628a04ba2a0d5554684cf527b
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962596B2

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