Sodium Carbonate → HCID 71548327, 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	2-chloro-5,7-dihydro-4-((S)-3-methylmorpholino)thieno[3,4-d]pyrimidine 6,6-dioxide	HCID 89494604	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	HCID 71548327	HCID 71548327	11%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of 2-chloro-5,7-dihydro-4-((S)-3-methylmorpholino)thieno[3,4-d]pyrimidine 6,6-dioxide (96 mg, 0.32 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 (106 mg, 0.35 mmol), and Na2CO3 (102 mg, 0.96 mmol) followed by PdCl2(dppf) (15 mg, 0.02 mmol). The resulting mixture was heated to 70° C. and stirred overnight 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 (Na2SO4) and the solvent removed to give crude product which was purified by preparative TLC (DCM/MeOH=20/1) to give the desired product as a yellow solid (15 mg, 11%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09242993B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-3d2677fad1a34b28ac2d9aa683f2b1ee
Source note	uspto-grants-2016_01