Sodium Carbonate → HCID 19050464, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)	HCID 3977284	—
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	HCID 19050464	HCID 19050464	43%

Reaction Steps

--Quantities: 5-bromo-2-iodopyrimidine 2 (1.23 g, 4.32 mmol), 4-octyloxyphenylboronic acid 7 (1.33 g, 5.18 mmol), tetrakis(triphenylphosphine)palladium (150 mg, 0.13 mmol), DME (30 ml), aqueous 2M sodium carbonate (30 ml). The experimental procedure was as described for compound 4 to yield the phenylpyrimidine 8 (0.67 g, 43%) (from EtOH), m.p. 95.0° C.; νmax /cm-1 (KBr) 2920, 1605, 1525, 1425, 1260, 1170, 1120 and 790; δ 0.90 (3H, t, Me), 1.20-1.55 (10H, m), 1.84 (2H, quint, OCH2CH2), 4.02 (2H, t, OCH2), 6.97 (2H, d, J 7, 3'- and 5'-H), 8.33 (2H, d, J 7, 2'- and 6'-H) and 8.76 (2H, s, 4- and 6-H); m/z 366 (M+), 364 (M+), 252 (M+ -C8H16) 250 (M+ -C8H16), 195 and 186.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05986096
Source dataset	uspto-grants-1999_11
ORD ID	ord-a5632c0c736044ed8ac462d34485431d
Source note	uspto-grants-1999_11