HCID 178497680, Verbindung → HCID 178497681, Verbindung

HRID 1108265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108265
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[CH:21]=[C:22]([C:35]([O:37][CH3:38])=[O:36])[N:23]([Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:24]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>CO.[Pd]>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([C:35]([O:37][CH3:38])=[O:36])[N:23]([Si:25]([CH:29]([CH3:30])[CH3:31])([CH:26]([CH3:27])[CH3:28])[CH:32]([CH3:34])[CH3:33])[CH:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Komponenten

4

Edukt 1

HCID 178497680HCID 178497680, Verbindung

Produkt 1

HCID 178497681HCID 178497681, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 4-[2-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethynyl]-1-triisopropylsilylpyrrole-2-carboxylate (550 mg, 1.0 mmol) and 10% palladium-on-carbon (220 mg) in methanol (45 mL) was stirred overnight under hydrogen (50 psi). The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo. The residue was dissolved in methylene chloride and filtered through a short silica gel column. The eluate was evaporated to give methyl 4-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]-1-triisopropylsilylpyrrole-2-carboxylate (524 mg, 94%). The analytical sample, mp 202-204° C., was obtained by column chromatography using chloroform:methanol (19:1): 1H NMR (CDCl3) δ 11.34 (br s, 1H), 7.85 (br s, 1H), 6.98 (s, 1H), 6.90 (s, 1H), 4.69 (s, 1H), 3.79 (s, 3H), 3.36 (br d, 1H, J=10.0 Hz), 2.99 (m, 1H), 2.83 (m, 1H), 2.59 (m, 2H), 2.12 (dd, 1H, J=15.6, 9.0 Hz), 1.90-1.50 (m, 6H), 1.30 (s, 9H), 1.11 (d, 18H, J=7.6 Hz).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride
  4. filtrationfiltered through a short silica gel column
  5. customThe eluate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-79bab5c82e024e24864ebc4917b36854
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066639

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