Ethanol → 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-carbamoyl-1-cyclopropyl-2-methyl-propyl)-amide

HRID 446937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446937
[C:1]([C:3]([CH3:32])([CH3:31])[CH:4]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([CH:20]3[CH2:22][CH2:21]3)[N:18]=2)[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:12]=1)=[O:10])[CH:5]1[CH2:7][CH2:6]1)#[N:2].CC[OH:35]>O.[PtH]1([P](O[H]O[P]1(C)C)(C)C)[P](O)(C)C>[C:1]([C:3]([CH3:32])([CH3:31])[CH:4]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([CH:20]3[CH2:22][CH2:21]3)[N:18]=2)[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[CH:12]=1)=[O:10])[CH:5]1[CH2:6][CH2:7]1)(=[O:35])[NH2:2]

Komponenten

4

Edukt 2

HCID 702EthanolHCID 670092382-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-cyano-1-cyclopropyl-2,2-dimethyl-ethyl)-amide

Produkt 1

HCID 673888952-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-carbamoyl-1-cyclopropyl-2-methyl-propyl)-amideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-cyano-1-cyclopropyl-2,2-dimethyl-ethyl)-amide (163 mg, 0.36 mmol) in EtOH (9 mL) and H2O (1 mL) was added [PtH(PMe2OH)(PMe2O)2H] (15 mg, 0.036 mmol). The reaction mixture was heated at reflux for 6 h. Additional catalyst (10 mg, 0.023 mmol) was added and heating was continued overnight. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes) to provide 108 mg (64%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-carbamoyl-1-cyclopropyl-2-methyl-propyl)-amide as a viscous colorless oil.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 h
  3. temperatureheating
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3904d24b61364957814d8aa9ff5fe3a3
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481541B2

Notizen zur Reaktion

Wird geladen…