Sodium Carbonate → HCID 71547383, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea	HCID 44119149	—
Reactant	HCID 62707601	HCID 62707601	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	HCID 71547383	HCID 71547383	27%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of (S)-2-chloro-4-(3-methylmorpholino)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine (100 mg, 0.35 mmol) in DME/H2O (4:1, 10 mL) was added 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (116 mg, 0.38 mmol) and Na2CO3 (111 mg, 1.05 mmol) followed by PdCl2(dppf) (15 mg, 0.02 mmol). The resulting mixture was stirred overnight at 70° C. under nitrogen. The solvent was removed under vacuum to give a residue which was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4 filtered and evaporated to give the crude product which was purified by preparative TLC (DCM/MeOH=20/1) to give the desired product as a yellow solid (40 mg, 27%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09242993B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-00c8fc515dc6405f8781ff8002b8027f
Source note	uspto-grants-2016_01