Hydrogen Peroxide → 4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-ynyl di-tert-butyl phosphate

Participants

Role	Name	HCID	Charge
Reactant	Hydrogen Peroxide	HCID 784	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	Di-tert-butyl N,N-Diisopropylphosphoramidite	HCID 853005	—
Reactant	4-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol	HCID 11950510	—
Reactant	HCID 178418441	HCID 178418441	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-ynyl di-tert-butyl phosphate	HCID 57713854	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

A solution of 4-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo [2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol (see example 2) (4.0 g) and 1-H-tetrazole (0.45 M in acetonitrile, 70 mL) in THF (160 mL) was treated with di-tert-butyl diisopropylphosphoramidite (16.4 mL) at rt for 2 h. The solution was cooled to 0° C. and treated with 30% aqueous H2O2 (11 mL) for 30 min. Work-up (EtOAc, aq. NaHCO3) and reverse-phase preparative HPLC gave the title compound, as a solid. HPLC Rt=6.13 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08093229B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-4c744ce333734f9187fff09fd72a4ccf
Source note	uspto-grants-2012_01