Cesium carbonate → HCID 66599878, compound

HRID 1621607Notes

Reaction equation

HRID 1621607 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:17]2[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)[CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[N:18]=2)[C:5]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[B-](F)(F)(F)[CH2:84][N:85]1[CH2:90][CH2:89][N:88]([CH3:91])[CH2:87][CH2:86]1.[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:24]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[C:19]2[N:18]=[C:17]([C:4]3[C:5]([NH:8][C:9]4[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=4)=[N:6][CH:7]=[C:2]([CH2:84][N:85]4[CH2:90][CH2:89][N:88]([CH3:91])[CH2:87][CH2:86]4)[CH:3]=3)[N:22]=[C:21]([CH3:23])[N:20]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphineHCID 45588174Potassium trifluoro[(4-methylpiperazin-1-yl)methyl]borate(1-)HCID 666119674-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 66599878HCID 66599878, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
140 °C

Procedure

A mixture of 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (160 mg, 0.274 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′,-tri-1-propyl-1,1′-biphenyl (X-Phos, 13.06 mg, 0.027 mmol), cesium carbonate (268 mg, 0.822 mmol), potassium 1-methyl-4-trifluoroboratomethylpiperazine (Frontier Scientific Co., 66.3 mg, 0.301 mmol) and palladium acetate (3.08 mg, 0.014 mmol) was purged with argon. The mixture was then treated with THF (1.0 mL) and water (0.1 mL) and heated under microwave irradiation at 140° C. for 30 min. The mixture was filtered through a short path of Celite® (diatomaceous earth), washed with EtOAc (×3), and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (pure DCM to 5% MeOH in DCM) to give N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-((4-methylpiperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (161 mg, 0.243 mmol, 89% yield) as a yellow syrup. m/z (ESI, +ve ion) 662.0 (M+H)+.

Workup

  1. customwas purged with argon
  2. additionThe mixture was then treated with THF (1.0 mL) and water (0.1 mL)
  3. filtrationThe mixture was filtered through a short path of Celite® (diatomaceous earth)
  4. washwashed with EtOAc (×3)
  5. concentrationconcentrated
  6. customchromatographed through a Redi-Sep pre-packed silica gel column (pure DCM to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-d8d5fcc65cff4e7399251459af80d70b
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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