Sodium Iodide → [6-chloro-2-(4-methoxy-benzylsulfanyl)-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Iodide	HCID 5238	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1H-Pyrazol-3-amine, 5-methyl-	HCID 93146	—
Reactant	4,6-Dichloro-2[[(4-methoxyphenyl)methyl]thio]pyrimidine	HCID 13413724	—
Solvent	1-Butanol	HCID 263	—
Product	[6-chloro-2-(4-methoxy-benzylsulfanyl)-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine	HCID 178419077	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of above-prepared 4,6-dichloro-2-(4-methoxy-benzylsulfanyl)-pyrimidine (915 mg, 3.04 mmol) and 3-amino-5-methylpyrazole (310 mg, 3.19 mmol) in BuOH (20 mL) is added diisopropylethylamine (0.56 mL, 3.19 mmol) followed by sodium iodide (455 mg, 3.04 mmol). The reaction mixture is stirred for 15 hours at 120° C. The solvent is removed in vacuo and the residue is purified by flash chromatography (SiO2, hexane/AcOEt gardient) to give [6-chloro-2-(4-methoxy-benzylsulfanyl)-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06653301B2
Source dataset	uspto-grants-2003_11
ORD ID	ord-f5e58e7d44744acbaf37c9619195532d
Source note	uspto-grants-2003_11