Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 889206Generated: October 26, 2026

Tributylamine → 3-(2-Methylcarbamoyl-pyrimidin 5-yl)acrylic acid benzyl ester

https://huagongshe.com/reaction/889206

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributylamineHCID 7622—
ReactantBenzyl acrylateHCID 75617—
ReactantTri-o-tolylphosphineHCID 80271—
Reactant5-bromo-N-methylpyrimidine-2-carboxamideHCID 66759926—
Catalystpalladium(II) acetateHCID 167845—
SolventDimethylformamideHCID 6228—
Product3-(2-Methylcarbamoyl-pyrimidin 5-yl)acrylic acid benzyl esterHCID 66759306—

Reaction Conditions

Temperature110 °C

Reaction Steps

To a solution of 5-bromo-N-methylpyrimidine-2-carboxamide (0.14 g, 0.64 mmol) in DMF (5 mL) was added acrylic acid benzyl ester (0.13 g, 0.78 mmol), Pd(OAc)2 (14.3 mg), tri-o-tolyl phosphine (49 mg, 0.16 mmol), tributyl amine (0.48 g, 2.59 mmol). The reaction mixture was heated in microwave oven at 110° C. for 1 h. The reaction mixture was cooled to room temperature, partitioned in water (50 mL) and ethyl acetate (50 mL). Ethyl acetate layer was separated, dried (MgSO4), concentrated to give 3-(2-methylcarbamoyl-pyrimidin 5-yl)acrylic acid benzyl ester as a solid, this was washed with hexanes and dried to give the 0.122 g of the product. LCMS (APCI) 298 (M+)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08252793B2
Source datasetuspto-grants-2012_08
ORD IDord-9abad802e6fa4c629df8d3603c22b2de
Source noteuspto-grants-2012_08