HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one | HCID 9878769 | — |
| Reactant | 3-methyl-5-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde | HCID 22135454 | — |
| Catalyst | Piperidine | HCID 8082 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 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 | HCID 69795299 | 100% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06610688B2 |
| Source dataset | uspto-grants-2003_08 |
| ORD ID | ord-001cea4d926f4c8f94e7a957dda82e83 |
| Source note | uspto-grants-2003_08 |