Triethylamine → (S)-2-amino-1-(4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)-3-methoxypropan-1-one

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	(2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acid	HCID 7016354	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	3-Bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine	HCID 86697434	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	(S)-2-amino-1-(4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)-3-methoxypropan-1-one	HCID 89810859	—

Reaction Steps

3-Bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine (300 mg, 1.1 mmol) taken up in 10 mL DMF. Boc-Ser(Me)-OH (280 mg, 1.3 mmol), HATU (368 mg, 1.6 mmol), and triethylamine (590 uL, 4.25 mmol) was added and stirred at room temp overnight. Reaction was diluted with DCM and washed with water. DCM layer was dried over magnesium sulfate reduced in vacuo. This was then taken up in 30% TFA in DCM solution and stirred at room temperature for 2 hours. It was then cooled to 0° C. and conc Aq NaOH added slowly until aqueous layer remains basic. DCM layer extracted dried over magnesium sulfate, reduced in vacuo for 405 mg crude product for further reaction as is. LRMS (ESI) m/z 383/385 [(M+H)]+, calc'd for C14H19BrN6O2: 383.25.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403832B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-c54ed2a45e6b482c89ec2d3b3a2e2e9d
Source note	uspto-grants-2016_08