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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 131576Generated: October 25, 2026

Water → 6-[2,3-Dihydro-2-oxo-1H-benzimidazol-1-ylmethyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid, methyl ester

https://huagongshe.com/reaction/131576

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
Reactant2-ChlorobenzimidazoleHCID 78572—
Reactant6-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-5-[4-(S)-hydroxy-2-isoxazolidinylcarbonyl]-3-methyl-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneHCID 10142559—
SolventEthyl AcetateHCID 8857—
Product6-[2,3-Dihydro-2-oxo-1H-benzimidazol-1-ylmethyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid, methyl esterHCID 86622711—

Reaction Steps

The product of example 3 part b) (0.5 g, 1.28 mmol), 2-chlorobenzimidazole (0.21 g, 1.37 mmol), potassium carbonate (0.36 g, 2.6 mmol) and DMF (10 ml) were stirred for 1.5 h. Ethyl acetate and water were added to the reaction mixture. The two phases were separated, the organic layer was dried (MgSO4) and then concentrated in vacuo. The residue was purified by biotage eluting with dichloromethane to give the sub-title compund as a pale yellow solid, 0.36 g (61%). δ 1HD6DMSO 0.83 and 0.91 (6H, d), 2.1-2.22 (1H,m), 3.38 (3H,s), 3.67 (2H,d), 4.1 (3H,s), 5.58 (2H,s), 7.26-7.38 (2H,m), 7.41-7.48 (1H,m) and 7.7-7.8 (1H,m).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07384950B2
Source datasetuspto-grants-2008_06
ORD IDord-56eb70ac79244e5a9cba5c5fb95804f0
Source noteuspto-grants-2008_06