Potassium Iodide → HCID 24963596, compound

HRID 1660897Notes

Reaction equation

HRID 1660897 reaction equation
[F:1][C:2]1[C:12](=[O:13])[N:11]([CH3:14])[C:5]2[N:6]=[CH:7][NH:8][C:9](=[O:10])[C:4]=2[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[F:23].[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:33][CH2:34][OH:35]>CN(C=O)C>[F:1][C:2]1[C:12](=[O:13])[N:11]([CH3:14])[C:5]2[N:6]=[CH:7][N:8]([CH2:33][CH2:34][OH:35])[C:9](=[O:10])[C:4]=2[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[F:23]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 136062038HCID 136062038, compound

Product 1

HCID 24963596HCID 24963596, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-fluoro-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione 17C (60 mg, 0.14 mmol, 1 eq) and potassium iodide (39 mg) in DMF (3 mL) was added cesium carbonate (135 mg, 0.42 mmol, 3 eq). The reaction mixture was stirred at ambient temperature for 5 minutes. 2-Bromoethanol (0.1 mL, 1.4 mmol, 10 eq) was then added and the reaction mixture was irradiated with microwave at 140° C. for 20 minutes. The reaction mixture was filtered and the filtrate was purified by preparatory LC/MS (30-55% CH3CN in H2O) to give 6-fluoro-5-(2-fluoro-4-iodophenylamino)-3-(2-hydroxyethyl)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (example 17) as an off-white solid (25 mg, 38% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.59 (s, 3H) 3.67 (dd, J=2.53, 1.26 Hz, 2H) 4.05 (t, J=5.05 Hz, 2H) 4.98 (br. s., 1H) 6.99 (td, J=8.65, 5.43 Hz, 1H) 7.53 (dd, J=8.34, 0.76 Hz, 1H) 7.68 (dd, J=10.36, 1.77 Hz, 1H) 8.55 (s, 1H) 10.22 (d, J=2.27 Hz, 1H). [M+H] calc'd for C16H13F2IN4O3, 475; found, 475.

Workup

  1. customthe reaction mixture was irradiated with microwave at 140° C. for 20 minutes
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was purified by preparatory LC/MS (30-55% CH3CN in H2O)

Sources & evidence

ORD record
ord-2a3e6206df994e488856ed63841f333d
Source dataset
uspto-grants-2011_10
Patent number
US08030317B2

Reaction notes

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