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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 397419Generated: October 29, 2026

4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → 4-(3-Chloro-4-fluoro-phenylamino)-5-[3-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-yl-methylene]-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-one

https://huagongshe.com/reaction/397419

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-oneHCID 9878769—
Reactant3-methyl-5-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehydeHCID 22135454—
CatalystPiperidineHCID 8082—
SolventEthanolHCID 702—
Product4-(3-Chloro-4-fluoro-phenylamino)-5-[3-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-yl-methylene]-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-oneHCID 69795299100%

Reaction Steps

A mixture of 4-(3-chloro-4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (70 mg, 0.25 mmol) and 3-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde (70.6 mg, 0.30 mmol) and piperidine (3 drops) in ethanol was stirred at room temperature for 4 days. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 124 mg (100%) of the title compound. 1H NMR (360 MHz, DMSO-d6) δ 13.41 (s, 1H, NH), 11.77 (br s, 1H, NH), 9.22 (br s, 1H), 8.32 (s, 1H), 7.72 (dd, J=2.7 & 6.6 Hz, 1H), 7.42 (m, 1H), 7.32-7.37 (m, 2H), 6.58 (d, J=1.8 Hz, 1H), 3.68 (m, 4H, 2×CH2), 2.36 (m, 4H, 2×CH2), 2.22 (s, 3H, CH3), 2.20 (s, 3H, CH3). MS 496 [M++1].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06610688B2
Source datasetuspto-grants-2003_08
ORD IDord-001cea4d926f4c8f94e7a957dda82e83
Source noteuspto-grants-2003_08