Sodium Carbonate → HCID 71547536, 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 89494611	HCID 89494611	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	HCID 71547536	HCID 71547536	80%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of 2-chloro-7,8-dihydro-4-((S)-3-methylmorpholino)-6H-thiopyrano[3,2-d]pyrimidine (150 mg, 0.53 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 (175 mg, 0.58 mmol) and Na2CO3 (170 mg, 1.60 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 and dried over anhydrous Na2SO4. The solvent was removed to give crude material which was purified by preparative TLC (DCM/MeOH=20/1) to give the desired productas a white solid (180 mg, 80%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09242993B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-8887779eb71a466dad350d02c8f908e3
Source note	uspto-grants-2016_01