Diisopropylethylamine → (2R)-2-[(2-amino-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-fluoro-4-methylpentan-1-ol

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(S)-7-chloro-5-((1-phenylethyl)thio)thiazolo[4,5-d]pyrimidin-2-amine	HCID 86622916	—
Reactant	(2R)-2-amino-4-fluoro-4-methylpentan-1-ol	HCID 86622919	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	(2R)-2-[(2-amino-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-fluoro-4-methylpentan-1-ol	HCID 86622918	34.3%

Reaction Conditions

Temperature	120 °C

Reaction Steps

DIPEA (0.83 mL, 4.75 mmol) was added to a solution of 7-chloro-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-2-amine (0.49 g, 1.52 mmol) and (2R)-2-amino-4-fluoro-4-methylpentan-1-ol (2 mmol) in NMP (2 mL) and the reaction mixture was stirred at 120° C. for 22 h. HPLC purification provided the title compound (0.22 g, 17% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07947693B2
Source dataset	uspto-grants-2011_05
ORD ID	ord-36514d7a74f54bbe87c53a52a5575bf3
Source note	uspto-grants-2011_05