1-Pentyne → 2-(4-Trifluoromethylphenyl)-5-pent-1-ynylpyrimidine

Participants

Role	Name	HCID	Charge
Reactant	1-Pentyne	HCID 12309	—
Reactant	Potassium Bromide	HCID 253877	—
Reactant	5-Bromo-2-(4-trifluoromethylphenyl)pyrimidine	HCID 23297051	—
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-Trifluoromethylphenyl)-5-pent-1-ynylpyrimidine	HCID 54064460	86.1%

Reaction Steps

--Quantities: 2-[4'-Trifluoromethylphenyl]-5-bromopyrimidine 10 (1.48 g, 4.88 mmol), pent-1-yne (0.96 ml, 9.76 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 to give the pentynylpyrimidine 40 (1.22 g, 86%) (from MeOH), m.p. 140.5° C., νmax /cm-1 (KBr) 2970, 2200(C≡C), 1520, 1430, 1325s, 1165, 1115, 1075 and 1015, ≡ 1.07(3H, t, Me), 1.68 (2H, sext, CH2CH3), 2.47 (2H, t, CH2C≡C), 7.74 (2H, d, 3'- and 5'-H), 8.55(2H, d, 2' and 6'-H) and 8.79 (2H, s, 4- and 6-H); m/z 290 (M+), 275, 261, 248, 172 and 152.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05986096
Source dataset	uspto-grants-1999_11
ORD ID	ord-e838e35061a040d09d61a8f3b5732be4
Source note	uspto-grants-1999_11