Diisopropylethylamine → ethyl 4-(3-(2-((tert-butoxycarbonylamino)methyl) acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate	HCID 71598790	—
Reactant	2-({[(Tert-butoxy)carbonyl]amino}methyl)prop-2-enoic acid	HCID 89613267	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	ethyl 4-(3-(2-((tert-butoxycarbonylamino)methyl) acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate	HCID 89630003	—

Reaction Steps

A mixture of ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (300 mg, 1.06 mmol), 2-((tert-butoxycarbonylamino)methyl)acrylic acid (321 mg, 1.60 mmol), HATU (606 mg, 1.59 mmol) and DIPEA (371 μL, 2.13 mmol) in DMF (5.0 mL) was stirred at room temperature for 3 hours. The resulting mixture was diluted with ethyl acetate (15 mL) and washed with saturated aqueous bicarbonate, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier to give ethyl 4-(3-(2-((tert-butoxycarbonylamino)methyl)acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C24H28N5O5 [M+H]+: 466, found 466.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08993756B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-7b18c8fec0c54502badc6c6a514642a8
Source note	uspto-grants-2015_03