Tert-Butylamine → 2-tert-Butylamino-4-[trimethylsilylethynyl]pyrimidine

HRID 1158229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158229
Cl[C:2]1[N:7]=[C:6]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=1.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([NH:18][C:2]1[N:7]=[C:6]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=1)([CH3:17])([CH3:16])[CH3:15]

Komponenten

3

Edukt 2

HCID 6385Tert-ButylamineHCID 115720232-Chloro-4-(2-(trimethylsilyl)ethynyl)pyrimidine

Produkt 1

HCID 121652332-tert-Butylamino-4-[trimethylsilylethynyl]pyrimidine

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-chloro-4-[trimethylsilylethynyl]pyrimidine (25 g, 0.12 mol) and tert-butylamine (100 mL) was heated to 80° C. for 2 d in a sealed tube. The mixture was cooled to rt and triturated with hexanes (100 mL). The resulting white precipitate was filtered and washed with hexanes. The filtrate was concentrated to give the crude product as a brown oil, which was used in the following reaction without further purification. TLC: Rf=0.40. mp 71-73° C. IR: 3293 (br, w), 2962 (w), 1569 (s). 1H NMR: 8.22 (d, J=5.0 Hz, 1H), 6.57 (d, J=5.0 Hz, 1H), 5.19 (s, 1H), 1.42 (s, 9H), 0.26 (s, 9H). 13C NMR: 162.38, 158.15, 150.95, 112.94, 102.77, 97.62, 51.41, 29.25, −0.11. Anal. Calcd for C13H21N3Si: C, 63.11; H, 8.56; N, 16.98. Found: C, 63.20; H, 8.52; N, 16.70.

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. customtriturated with hexanes (100 mL)
  3. filtrationThe resulting white precipitate was filtered
  4. washwashed with hexanes
  5. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-b49680ac1e2241cba7a48d34a48cd047
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807832B2

Notizen zur Reaktion

Wird geladen…