Pyridine → 1-{3-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl}-5-fluoro-1h-pyrimidine-2,4-dione

HRID 1827009Notes

Reaction equation

HRID 1827009 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:21])[N:11]([C:18](Cl)=[O:19])[C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[F:22][C:23]1[C:24](=[O:30])[NH:25][C:26](=[O:29])[NH:27][CH:28]=1.N1C=CC=CC=1>C1COCC1>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:21])[N:11]([C:18]([N:27]2[CH:28]=[C:23]([F:22])[C:24](=[O:30])[NH:25][C:26]2=[O:29])=[O:19])[C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 33855-FluorouracilHCID 879046953-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl chloride

Product 1

HCID 601112331-{3-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl}-5-fluoro-1h-pyrimidine-2,4-dioneYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a reaction mixture of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl chloride (75 mg, 0.25 mmol), 5-fluorouracil (75 mg, 0.58 mmol), and 0.5 mL of pyridine in 2.0 mL of THF was stirred at room temperature for 1 h and filtered. The solid was then washed with THF, acetone, methanol, and ether to give 34 mg (36%) of 1-{3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl}-5-fluoro-1H-pyrimidine-2,4-dione as a light yellow solid. 1HNMR (400 MHz, DMSO-d6) δ 12.22 (d, J=4.69 Hz, 1H, CONHCO), 12.19 (s, br, 1H, NH-1′), 8.33 (d, J=6.64 Hz, 1H, H-6″), 7.92–7.94 (m, 1H, H-4), 7.74–7.76 (m, 1H, H-7), 7.71 (s, 1H, H-vinyl), 7.26–7.29 (m, 2H, H-5, 6), 6.16 (s, br, 1H, H-4′), 2.47 (s, 3H, CH3), and 2.35 (s, 3H, CH3).

Workup

  1. filtrationfiltered
  2. washThe solid was then washed with THF, acetone, methanol, and ether

Sources & evidence

ORD record
ord-29e37855906e491f8ad20778b7dd639a
Source dataset
uspto-grants-2006_05
Patent number
US07053114B2

Reaction notes

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