Sodium Azide → (R)-N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-N-methyl-5-(2H-tetrazol-5-yl)pyridin-2-amine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Azide	HCID 33557	—
Reactant	Ammonia chloride	HCID 20976574	—
Reactant	(R)-6-((1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)(methyl)amino)nicotinonitrile	HCID 66765754	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(R)-N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-N-methyl-5-(2H-tetrazol-5-yl)pyridin-2-amine	HCID 86692153	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of (R)-6-((1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)(methyl)amino)nicotinonitrile (100 mg, 0.3 mmol), ammonia chloride (84 mg, 1.57 mmol) and sodium azide (108 mg, 1.66 mmol) in N,N-dimethylformamide (5.0 mL) was stirred at 120° C. for 16 h. The volatile was removed under vacuum and the residue was purified by chromatography on silica gel to give the title compound. MS (m/z): 363.0 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09346810B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-ba07618c7dca45be825a729a72254b9b
Source note	uspto-grants-2016_05