HCID 66600402, compound → 4-(2-Fluoro-5-(tetrahydro-2H-pyran-4-YL)pyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621972Notes

Reaction equation

HRID 1621972 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([C:14]3[N:19]=[C:18]([CH3:20])[N:17]=[C:16]([N:21]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[CH2:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[N:15]=3)[C:10]([F:13])=[N:11][CH:12]=2)[CH2:3][CH2:2]1.[H][H]>CCO.CCOC(C)=O.[OH-].[Pd+2].[OH-]>[F:13][C:10]1[C:9]([C:14]2[N:19]=[C:18]([CH3:20])[N:17]=[C:16]([N:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[N:15]=2)=[CH:8][C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:12][N:11]=1

Participants

6

Reactant 2

HCID 66600402HCID 66600402, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 666000634-(2-Fluoro-5-(tetrahydro-2H-pyran-4-YL)pyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineYield 76.3%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(5-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (300 mg, 0.569 mmol) in 5 mL of EtOH and 5 mL of EtOAc was placed with palladium hydroxide (20% wt.) (80 mg, 0.114 mmol) and hydrogenated with a balloon full of hydrogen. After 18 h, the mixture was filtered through a pad of Celite® (diatomaceous earth) and rinsed with 2×10 mL of EtOAc. The filtrate was concentrated and the residue was purified on a silica gel column and eluted with 20-65% EtOAc in hexanes to provide 4-(2-fluoro-5-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (230 mg, 76% yield) as an off white amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.36 (dd, J=9.4, 1.6 Hz, 1H), 8.30 (d, J=1.9 Hz, 1H), 7.24 (m, 4H), 6.90 (m, 4H), 4.79 (s, 2H), 4.75 (s, 2H), 3.94 (m, 2H), 3.74 (s, 3H), 3.72 (s, 3H), 3.45 (m, 2H), 2.95 (m, 1H), 2.47 (s, 3H), 1.70 (m, 4H). m/z (ESI, positive ion) 530.3 (M+H)+.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite® (diatomaceous earth)
  2. washrinsed with 2×10 mL of EtOAc
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified on a silica gel column
  5. washeluted with 20-65% EtOAc in hexanes

Sources & evidence

ORD record
ord-f64535ad424b4ff9a5bf2cafa8dc418c
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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