Potassium Carbonate → N-(3-(5-methyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide

HRID 527411Notes

Reaction equation

HRID 527411 reaction equation
[CH3:1][C:2]1[C:11]2[CH:10]=[N:9][C:8]([S:12][CH3:13])=[N:7][C:6]=2[N:5]([C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:24])[CH:22]=[CH2:23])[CH:17]=[CH:18][CH:19]=2)[C:4](=[O:25])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:1][C:2]1[C:11]2[CH:10]=[N:9][C:8]([S:12]([CH3:13])=[O:34])=[N:7][C:6]=2[N:5]([C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:24])[CH:22]=[CH2:23])[CH:17]=[CH:18][CH:19]=2)[C:4](=[O:25])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 86732025N-(3-(5-methyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide

Product 1

HCID 86732024N-(3-(5-methyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamideYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Steps 2 and 3. To a suspension of N-(3-(5-methyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide (5a; 5.15 g, 14.63 mmol) in DCM (100 mL) at 0° C. was added MCPBA (77 wt. %, 3.51 g, 15.65 mmol) in one portion. The resulting suspension was stirred at 0° C. for 1 h. The reaction mixture was diluted with DCM (100 mL) and treated with an ice cold solution of 1.0 M K2CO3. The aqueous layer was extracted with DCM (2×100 mL). The organic extracts were dried over Na2SO4, filtered and concentrated affording crude N-(3-(5-methyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide (5b; 1.09 g, 2.96 mmol, 20% yield) as a light yellow foam. The aqueous layer contained suspended material so it was filtered through a medium porosity sintered glass frit and washed with water and Et2O affording additional N-(3-(5-methyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide (5b; 4.59 g, 12.46 mmol, 85% yield) as a light yellow free-flowing solid after drying under vacuum. m/z (ESI, +ve ion) 369.1 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.33 (1H, s), 9.33 (1H, s), 7.69-7.76 (1H, m), 7.66 (1H, d, J=1.8 Hz), 7.43-7.52 (1H, m), 6.97-7.07 (1H, m), 6.81 (1H, d, J=1.4 Hz), 6.44 (1H, dd, J=16.9, 10.1 Hz), 6.25 (1H, dd, J=16.9, 1.9 Hz), 5.69-5.81 (1H, m), 2.71 (3H, s), 2.59 (3H, d, J=1.2 Hz).

Workup

  1. extractionThe aqueous layer was extracted with DCM (2×100 mL)
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4df7988fc45e4e399c82d1d32bd90e40
Source dataset
uspto-grants-2016_05
Patent number
US09346801B2

Reaction notes

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