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

Participants

Role	Name	HCID	Charge
Reactant	1-Pentyne	HCID 12309	—
Reactant	5-Bromo-2-(4-fluorophenyl)pyrimidine	HCID 23297064	—
Reactant	2-(2',3'-Difluoro-4'-octyloxyphenyl)-5-non-1-ynylpyrimidine	HCID 54455102	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Diisopropylamine	HCID 7912	—
Product	2-(4'-Fluorophenyl)-5-pent-1-ynylpyrimidine	HCID 19386263	87%

Reaction Steps

--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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05986096
Source dataset	uspto-grants-1999_11
ORD ID	ord-ed1bb7e6f9554ff6afd79009163be1ae
Source note	uspto-grants-1999_11