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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	L-Leucinol	HCID 111307	—
Reactant	(S)-7-chloro-5-((1-phenylethyl)thio)thiazolo[4,5-d]pyrimidin-2-amine	HCID 86622916	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	2-[(2-amino-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol	HCID 86622917	55.1%

Reaction Conditions

Temperature	120 °C

Reaction Steps

DIPEA (400 mg, 3 mmol) and D -leucinol (400 mg, 3.4 mmol) were added to 7-chloro-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-2-amine (300 mg, 0.9 mmol) in NMP (6 mL) and the mixture was heated to 120° C. for 24 h. The mixture was poured into water and extracted with ethyl acetate. The organic phase was dried (MgSO4), evaporated and the residue was purified by flash column chromatography (EtOAc) to give the title compound (200 mg, 54% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07947693B2
Source dataset	uspto-grants-2011_05
ORD ID	ord-b03268826cb9471885be0d0350c582a9
Source note	uspto-grants-2011_05