Triphenylphosphine → Tert-butyl (S)-3-(4-chloro-5-iodo-7H-pyrrolo[2,3-D]pyrimidin-7-YL)pyrrolidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropyl azodicarboxylate	HCID 5363146	—
Reactant	tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate	HCID 6544479	—
Reactant	6-Chloro-7-iodo-7-deazapurine	HCID 14809281	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Tert-butyl (S)-3-(4-chloro-5-iodo-7H-pyrrolo[2,3-D]pyrimidin-7-YL)pyrrolidine-1-carboxylate	HCID 44141157	64.8%

Reaction Steps

DIAD (1.41 ml) was added to a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.00 g), (R)—N-Boc-3-pyrrolidinol (1.01 g), and triphenylphosphine (1.88 g) in tetrahydrofuran (40 ml), and the reaction mixture was stirred for 1 hour. The reaction mixture was concentrated and washed with ethyl acetate to obtain the title compound as a white solid (1.04 g). Physical properties: m/z [M+H]+ 448.9

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09108973B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-fa9bbd0c05b942b592eb562f8feb0e53
Source note	uspto-grants-2015_08