Phenylsilane → 2-Amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 524841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524841
[NH2:1][C:2]1[C:13]([C:14]([O:16]CC=C)=[O:15])=[C:5]2[N:6]=[CH:7][C:8]([CH2:10][C:11]#[N:12])=[CH:9][N:4]2[N:3]=1.C1([SiH3])C=CC=CC=1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:13]([C:14]([OH:16])=[O:15])=[C:5]2[N:6]=[CH:7][C:8]([CH2:10][C:11]#[N:12])=[CH:9][N:4]2[N:3]=1

Komponenten

5

Edukt 2

HCID 12752PhenylsilaneHCID 86720890Allyl 2-amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate

Produkt 1

HCID 867208922-Amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of allyl 2-amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate 4c (10.2 g, 39.65 mmol) in DCM (350 mL) was added phenylsilane (8.581 g, 9.773 mL, 79.3 mmol), followed by Pd(PPh3)4 (1.5 g, 1.298 mmol). The reaction was stirred at room temperature for 2 h. The reaction mixture was filtered and the solid was washed with DCM and dried under vacuum to provide 2-amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 5c as a yellow solid (8.61 g, 100% yield).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with DCM
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e4fd344a4e2e44208d4de2a6906678f0
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340546B2

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