Cesium carbonate → 4-(3-Chloropyridin-4-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1811918Notes

Reaction equation

HRID 1811918 reaction equation
I[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1.[Cl:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][C:34]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][C:34]=1[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 38618773-Chloro-4-pyridineboronic acidHCID 601556234-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 666002154-(3-Chloropyridin-4-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 3

HCID 178478230HCID 178478230, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (306 mg, 0.642 mmol), 3-chloropyridine-4-boronic acid (101 mg, 0.642 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (52.4 mg, 0.064 mmol) and cesium carbonate (251 mg, 0.770 mmol) in dioxane (6 mL) and water (1 mL) was stirred at 90° C. for 1 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow glass. The crude product was purified by silica gel chromatography eluting with 50% EtOAc/hexanes to give the product as a glass. 1H NMR (300 MHz, CDCl3) δ 8.69 (s, 1H); 8.58 (d, J=4.97 Hz, 1H); 7.71 (d, J=4.82 Hz, 1H); 7.10-7.26 (m, 4H); 6.86 (t, J=8.77 Hz, 4H); 4.80 (s, 4H); 3.81 (s, 3H); 3.80 (s, 3H); 2.56 (s, 3H). m/z (ESI, +ve ion) 462.0 (M+H)+.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. extractionextracted with EtOAc (2×30 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material as a light-yellow glass
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-08dc5ff7977b4dae90843214da7598ca
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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