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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1778512Generated: November 2, 2026

2-Chlorobenzaldehyde → HCID 118409653, compound

https://huagongshe.com/reaction/1778512

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-ChlorobenzaldehydeHCID 6996—
ReactantEthyl AcetoacetateHCID 8868—
Reactant2-Chloro-4-fluorobenzaldehydeHCID 145024—
ReactantMethyl (R)-6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateHCID 89995948—
ProductHCID 118409653HCID 118409653—

Reaction Steps

The title compounds were prepared in analogy to Example 86 starting from methyl 2-(6-fluoro-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)acetate 100a (100 mg) and ethyl (4R)-6-(bromomethyl)-4-(2-chloro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate 102a (215 mg). The crude product was purified by silica gel chromatography first, and then by preparative HPLC to give Example 102 (27 mg), and Example 103 (21 mg). Ethyl (4R)-6-(bromomethyl)-4-(2-chloro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate 102a was prepared in analogy to compound C with procedures shown in Example 1 by using ethyl acetoacetate and 2-chloro-benzaldehyde instead of methyl acetoacetate and 2-chloro-4-fluoro-benzaldehyde in the three component reaction.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09266904B2
Source datasetuspto-grants-2016_02
ORD IDord-1fc731ccc2074f5aabdca3ed928f14bd
Source noteuspto-grants-2016_02