Sodium Carbonate → benzyl[2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	N-benzyl-2-chloropyrimidin-4-amine	HCID 1712887	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 49758959	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	benzyl[2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amine	HCID 11558506	11%

Reaction Conditions

Temperature	160 °C

Reaction Steps

A solution of 4 (0.36 g, 0.09 mmol), 10 (0.028 g, 0.108 mmol), 2.0M Na2CO3 (0.108ml, 0.271 mmol) and catalytic PdCl2(PPh3)2 in 1 ml of DMSO was heated in the microwave at 160° C. for 5 minutes resulting in conversion to tosyl protected product by LC/MS (M+1)=456. NaOtBu (0.026 g, 0.271 mmol) was added to the reaction and it was heated in the microwave for 5 minutes at 160° C. resulting in complete conversion to product 11. The reaction was filtered and purified by preparative HPLC giving 0.0032 g of 11 as a white solid in 11% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987454B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-add450f7fa6f4de889316358b2968af4
Source note	uspto-grants-2015_03