1-Chloro-2,4-Dinitrobenzene → 3-(2,4-dinitrophenyl)-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 1660901Notes

Reaction equation

HRID 1660901 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]2[C:18](=[O:20])[NH:17][CH:16]=[N:15][C:14]=2[N:13]([CH3:21])[C:12](=[O:22])[CH:11]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:33]=1[N+:41]([O-:43])=[O:42]>CN(C=O)C>[N+:38]([C:35]1[CH:34]=[C:33]([N+:41]([O-:43])=[O:42])[CH:32]=[CH:37][C:36]=1[N:17]1[C:18](=[O:20])[C:19]2[C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=3[F:1])=[CH:11][C:12](=[O:22])[N:13]([CH3:21])[C:14]=2[N:15]=[CH:16]1)([O-:40])=[O:39]

Participants

6

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1357417325-((2-Fluoro-4-iodophenyl)amino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Product 1

HCID 581919293-(2,4-dinitrophenyl)-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione 5F (41 mg, 0.1 mmol, 1 eq) and catalytic amount of potassium iodide in DMF (1 mL) was added potassium carbonate (21 mg, 0.15 mmol, 1.5 eq). The reaction mixture was stirred at ambient temperature for 5 minutes. 1-Chloro-2,4-dinitrobenzene (22 mg, 0.11 mmol, 1.1 eq) was then added and the reaction mixture was irradiated with microwave at 80° C. for 30 minutes and then at 100° C. for 30 minutes. The reaction mixture was filtered and the filtrate was purified by preparatory LC/MS (50-75% CH3CN in H2O) to give 3-(2,4-dinitrophenyl)-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione compound 24A as a yellow solid (18 mg, 31% yield). 1H NMR (400 MHz, CDCl3) δ ppm 3.78 (s, 3H) 6.09 (s, 1H) 7.17-7.24 (m, 1H) 7.52 (d, J=8.34 Hz, 2H) 7.72-7.80 (m, 1H) 8.23 (s, 1H) 8.75 (dd, J=8.46, 2.65 Hz, 1H) 9.12 (d, J=2.53 Hz, 1H) 9.83 (s, 1H). [M+H] calc'd for C20H12FIN6O6, 579; found, 579.

Workup

  1. customthe reaction mixture was irradiated with microwave at 80° C. for 30 minutes
  2. waitat 100° C. for 30 minutes
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was purified by preparatory LC/MS (50-75% CH3CN in H2O)

Sources & evidence

ORD record
ord-b1e394459ddf4706a923e8f52d8789c0
Source dataset
uspto-grants-2011_10
Patent number
US08030317B2

Reaction notes

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