Hydrochloric Acid → [2-(2-Chloro-6-fluoro-phenyl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine hydrochloride

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	4-Nitrophenethylamine	HCID 95153	—
Reactant	3-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenol	HCID 11494834	—
Reactant	[2-(2-Chloro-6-fluoro-phenyl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine	HCID 57636022	—
Solvent	Ethanol	HCID 702	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	Acetonitrile	HCID 6342	—
Product	[2-(2-Chloro-6-fluoro-phenyl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine hydrochloride	HCID 69073584	60%

Reaction Steps

By proceeding in a similar manner to Example 43(b) but (i) substituting 2-(2-chloro-6-fluoro-phenyl)-ethylamine for 2-(4-nitro-phenyl)-ethylamine, acetonitrile for EtOH as solvent in Step 3 there is prepared [2-(2-chloro-6-fluoro-phenyl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine which is dissolved in ether and treated with 1 M hydrogen chloride in ether to afford [2-(2-chloro-6-fluoro-phenyl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine hydrochloride [51 mg, 60%, Example 43(d)] as a solid. LC/MS: RT=2.82 minutes MS: 388 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □7.12-7.48 (7H, m), 6.6 (1H, s), 3.99 (3H, s), 3.82 (3H, s), 3.67 (2H, m), 3.07 (2H, m).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07517889B2
Source dataset	uspto-grants-2009_04
ORD ID	ord-cdd4a730f6c74f65aebb6c8d87fce307
Source note	uspto-grants-2009_04