Ethyl Acetate → 4-i-Propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-amide

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	4,6-Dichloro-5-(2-methoxyphenoxy)-2-(pyridin-4-YL)pyrimidine	HCID 11175458	—
Reactant	Sulfamide, [4-(1-methylethyl)phenyl]-(9CI)	HCID 21041219	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-i-Propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-amide	HCID 10279868	26.7%

Reaction Conditions

Temperature	45 °C

Reaction Steps

To a solution of 4-i-propyl-phenyl sulfamic acid amide (642 mg; Referential Example 17) in DMF (9 ml) was added sodium hydride (250 mg). The mixture was warmed to 45° C. for 30 min. Then, 4,6-dichloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (1.044 g) was added and the reaction mixture was stirred for 60 h at r.t. After acidic work up and chromatography over silicagel with Hex/EtOAc=2/5, 4-i-propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-amide (0.42 g) can be isolated.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07094781B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-44158203bde3470ebd74d37d12d5fe1d
Source note	uspto-grants-2006_08