1-Pentyne → 2-(4'-Fluorophenyl)-5-pent-1-ynylpyrimidine

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	1-Pentyne	HCID 12309	—
Edukt	5-Bromo-2-(4-fluorophenyl)pyrimidine	HCID 23297064	—
Edukt	2-(2',3'-Difluoro-4'-octyloxyphenyl)-5-non-1-ynylpyrimidine	HCID 54455102	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Katalysator	HCID 178418397	HCID 178418397	—
Lösungsmittel	Diisopropylamine	HCID 7912	—
Produkt	2-(4'-Fluorophenyl)-5-pent-1-ynylpyrimidine	HCID 19386263	87%

Reaktionsschritte

--Quantities: 2-(4'-fluorophenyl)-5-bromo-pyrimidine 20 (1.48 g, 4.88 mmol), pent-1-yne (0.98 ml, 10 mmol), tetrakis(triphenylphosphine)palladium (350 mg, 0.30 mmol), copper(I) iodide (57 mg, 0.30 mmol), diisopropylamine (20 ml). The experimental procedure was as described for compound 38. The crude product was purified by flash chromatography (8% ethyl acetate-light petroleum) to give the fluorophenylpyrimidine 42 (1.02 g, 85%), m.p. 51° C.; νmax /cm-1 (KBr) 2960, 2870, 2220, 1600, 1510, 1430, 1220, 1150 and 855; δ 1.07 (3H, t, Me), 1.68 (2H, sext, CH2CH3), 2.47 (2H, t, CH2C≡C), 7.18 (2H, t, 3'- and 5'-H), 8.44 (2H, dd, 2'- and 6'-H) and 8.75 (2H, s, 4- and 6-H); m/z 240 (M+), 225, 212, 198, 184, 171 and 118.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US05986096
Quelldatensatz	uspto-grants-1999_11
ORD ID	ord-ed1bb7e6f9554ff6afd79009163be1ae
Quellennotiz	uspto-grants-1999_11