Sodium Carbonate → HCID 59548392, compound

HRID 1621396Notes

Reaction equation

HRID 1621396 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:26]=[C:27](B(O)O)[C:28]([F:31])=[N:29][CH:30]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.O1CCOCC1>[F:31][C:28]1[N:29]=[CH:30][C:25]([CH2:24][N:21]2[CH2:20][CH2:19][N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH2:23][CH2:22]2)=[CH:26][C:27]=1[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 127064372-Chloro-4-methyl-6-(methylthio)-1,3,5-triazineHCID 59548218(5-((4-(tert-Butoxycarbonyl)piperazin-1-yl)methyl)-2-fluoropyridin-3-yl)boronic acid

Product 1

HCID 59548392HCID 59548392, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1,4-dioxane (15 mL) and H2O (3.00 mL) were added to a mixture of 2-chloro-4-methyl-6-(methylthio)-1,3,5-triazine (0.560 g, 3.19 mmol), 5-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)-2-fluoropyridin-3-ylboronic acid (1.03 g, 3.04 mmol), Na2CO3 (0.805 g, 7.59 mmol), and Pd(Ph3P)4 (0.175 g, 0.152 mmol) and the stirred suspension was heated at 80° C. overnight. After cooling, the mixture was passed a short plug of Na2SO4, washed with EtOAc(×2) and concentrated. The residue was adsorbed onto a plug of silica gel and chromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr., pre-packed silica gel column (hexanes to 30% ethyl acetate in hexanes) to give tert-butyl 4-((6-fluoro-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyridin-3-yl)methyl)piperazine-1-carboxylate (0.9676 g, 74%) as a white solid. LCMS (API-ES) m/z 435 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 8.57 (d, J=9.00 Hz, 1H) 8.30 (s, 1H) 3.58 (s, 2H) 3.44 (br. s., 4H) 2.66 (s, 3H) 2.64 (s, 3H) 2.43 (d, J=4.50 Hz, 4H) 1.46 (s, 9H).

Workup

  1. temperatureAfter cooling
  2. washwashed with EtOAc(×2)
  3. concentrationconcentrated
  4. customchromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr

Sources & evidence

ORD record
ord-c80493f6659c4f0daaf671d5250f38c9
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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