Sodium Carbonate → 2-(2'-Fluoro-4'-benzyloxyphenyl)-5-bromopyrimidine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-Benzyloxy-2-fluorophenylboronic acid	HCID 2737786	—
Reactant	5-Bromo-2-iodopyrimidine	HCID 7006651	—
Reactant	2-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine	HCID 23297043	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	2-(2'-Fluoro-4'-benzyloxyphenyl)-5-bromopyrimidine	HCID 54022540	53%

Reaction Steps

--Quantities: 5-bromo-2-iodopyrimidine 2 (5.05 g, 17.7 mmol), 2-fluoro-4-benzyloxyphenylboronic acid 27 (4.84 g, 19.7 mmol), tetrakis(triphenylphosphine)palladium (680 mg, 0.59 mmol), 2M sodium carbonate (50 ml), DME (50 ml). The experimental procedure was as described for compound 4 to yield the benzyloxyfluorophenylpyrimidine 28 (3.34 g, 53%) (from MeOH), m.p. 124.2° C.; νmax /cm-1 (KBr) 3030, 2860, 1615s, 1430, 1420, 1320, 1215, 1020 and 830, δ 5.22 (2H, s, CH2), 6.75-6.89 (2H, m, 3'- and 5'-H), 7.32-7.48 (5H, m, Ph), 8.06 (1H, t, 6'-H) and 8.85 (2H, s, 4-and 6-H); m/z 360 (M+), 358 (M+), 269 (M+ -PhCH2), 267 (M+ -PhCH2), 247, 221 and 91.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05986096
Source dataset	uspto-grants-1999_11
ORD ID	ord-0c5c90137cc74f7d8fec43641ed1e557
Source note	uspto-grants-1999_11