Sodium Bicarbonate → 3-[8-(2,6-Difluoro-phenyl)-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-propyl-benzamide

HRID 1806560Notes

Reaction equation

HRID 1806560 reaction equation
Cl[C:2]1[C:3]2[CH:13]=[CH:12][C:11](=[O:14])[N:10]([C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])[C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1.[CH3:23][C:24]1[CH:35]=[CH:34][C:27]([C:28]([NH:30][CH2:31][CH2:32][CH3:33])=[O:29])=[CH:26][C:25]=1B1OC(C)(C)C(C)(C)O1.C(=O)(O)[O-].[Na+]>C(O)(C)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([F:21])[C:15]=1[N:10]1[C:4]2[N:5]=[C:6]([S:8][CH3:9])[N:7]=[C:2]([C:25]3[CH:26]=[C:27]([CH:34]=[CH:35][C:24]=3[CH3:23])[C:28]([NH:30][CH2:31][CH2:32][CH3:33])=[O:29])[C:3]=2[CH:13]=[CH:12][C:11]1=[O:14]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 119515134-Chloro-2-methylsulfanyl-8-(2,6-difluorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 574345484-methyl-N-propyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 1

HCID 592126693-[8-(2,6-Difluoro-phenyl)-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-propyl-benzamide

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To 4-chloro-8-(2,6-difluoro-phenyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7 one (200 mg, 0.589 mmol, 1 eq) and 4-methyl-N-propyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (268 mg, 0.883 mmol, 1.5 eq) in isopropanol (6 mL) was added sodium bicarbonate (148 mg, 1.76 mmol, 3 eq) in water (1.5 mL). The reaction mixture was then purged with nitrogen followed by addition of tetrakis(triphenylphosphine)-palladium(0) (34 mg, 0.029 mmol, 5 mol %). The mixture was then heated to about 80° C. overnight. The mixture was then allowed to cool to room temperature before the solvent was removed in vacuo. The residue was then purified on the Flashmaster 2™: LC-MS m/z 481 (M+H)+, 3.34 min (ret time).

Workup

  1. customThe reaction mixture was then purged with nitrogen
  2. temperatureto cool to room temperature before the solvent
  3. customwas removed in vacuo
  4. customThe residue was then purified on the Flashmaster 2™
  5. customLC-MS m/z 481 (M+H)+, 3.34 min (ret time)

Sources & evidence

ORD record
ord-26372320f9934558bde3d121cfd8e55a
Source dataset
uspto-grants-2013_01
Patent number
US08354416B2

Reaction notes

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