Triethylamine → (R)-((S)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxy-2-methylbut-3-ynyl) 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

https://huagongshe.com/reaction/1984117

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chloride, (S)-(+)-	HCID 2724611	—
Reactant	Dichloromethane ethylacetate	HCID 21226138	—
Reactant	(S)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol	HCID 57713819	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(R)-((S)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxy-2-methylbut-3-ynyl) 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate	HCID 57713806	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

A mixture of (S)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol (see example 52) (18 mg), (S)-(+)-α-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride (45 μL), and Et3N (50 μL) in THF (3.0 mL) was heated to 70° C. for 2 h, and then to 40° C. overnight. Preparative TLC (EtOAc/DCM 25:65) gave the title compound, as a solid. HPLC Rt=6.45 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07544672B2
Source dataset	uspto-grants-2009_06
ORD ID	ord-4681784d745a429aba815bd2ff36293b
Source note	uspto-grants-2009_06