Sodium Carbonate → (R)-tert-butyl 3-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-Phenoxyphenylboronic acid	HCID 2734377	—
Reactant	(R)-tert-butyl 3-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate	HCID 71014221	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	(R)-tert-butyl 3-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate	HCID 86714513	55.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of (R)-tert-butyl 3-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate (250 mg, 0.56 mmol), 4-phenoxyphenylboronic acid (133 mg, 0.62 mmol), Pd(PPh3)4 (100 mg) and Na2CO3 (150 mg, 1.41 mmol) in dioxane/H2O (40/10 ml) was stirred at 100° C. for 4 h. The reaction mixture was concentrated and purified by Pre-TLC to obtain (R)-tert-butyl 3-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate (150 mg, 55% in yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08759358B1
Source dataset	uspto-grants-2014_06
ORD ID	ord-30a9b7fac2d748f99a4eb2ca392be4b3
Source note	uspto-grants-2014_06