2-Aminothiazole → 2-chloro-6-methyl-N-(1,3-thiazol-2-yl)pyrimidin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	2-Aminothiazole	HCID 2155	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	2,4-Dichloro-6-methylpyrimidine	HCID 79471	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-chloro-6-methyl-N-(1,3-thiazol-2-yl)pyrimidin-4-amine	HCID 57440763	—

Reaction Conditions

Temperature	85 °C

Reaction Steps

To the mixture of 2,4-dichloro-6-methylpyrimidine (507.7 mg), 1,3-thiazol-2-amine (345.0 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (289.1 mg) and K3PO4 (936.3 mg) in dioxane (20 ml) was added Pd2(dba)3 CHCl3 (255.9 mg). And the suspension was stirred at 85° C. overnight. The mixture was cooled to room temperature. The insoluble material was filtered off and washed with EtOAc. The filtrate was poured into saturated aqueous solution of NaHCO3 and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4 and concentrated. The residue was purified with silica gel column chromatography (eluent: CHCl3/MeOH=98/2˜90/10) to give 2-chloro-6-methyl-N-(1,3-thiazol-2-yl)pyrimidin-4-amine as an orange solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08367690B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-6f33fe44863944ffb1c8649ddccb4ffb
Source note	uspto-grants-2013_02