Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1177142Generated: October 30, 2026

Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate → 4-(2-Dimethylcarbamoyl-pyrimidin-5-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

https://huagongshe.com/reaction/1177142

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylateHCID 25067323—
Reactant5-bromo-N,N-dimethylpyrimidine-2-carboxamideHCID 59559990—
Reactant4-(6-Dimethylcarbamoyl-pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterHCID 59560224—
Product4-(2-Dimethylcarbamoyl-pyrimidin-5-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterHCID 59559900—

Reaction Steps

The title compound was prepared in a similar manner as described for Intermediate 161b, from 5-bromo-pyrimidine-2-carboxylic acid dimethylamide (164a) (271 mg, 1.18 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) (262 mg, 1.18 mmol) to give a white foam (110 mg, 25% yield). 1H NMR (400 MHz, CDCl3) δ 8.50 (s, 2 H) 7.24-7.36 (m, 1 H) 7.20 (s, 1 H) 3.88 (s, 3 H) 3.17 (s, 3 H) 3.00 (s, 3 H) 2.95 (s, 2 H) 1.51 (s, 6 H); LCMS for C19H21N3O5 m/z 372.00 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07842713B2
Source datasetuspto-grants-2010_11
ORD IDord-3faf1c64b5e049bbaadf2889c60fbb5b
Source noteuspto-grants-2010_11