Methanol → 1-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol

HRID 1812337Notes

Reaction equation

HRID 1812337 reaction equation
[CH3:1][O:2][C:3]1[CH:45]=[CH:44][C:6]([CH2:7][N:8]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([C:32](=[O:34])[CH3:33])[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=3)[N:10]=2)=[CH:5][CH:4]=1.[B-].[Na+].CO>C(Cl)Cl>[CH3:43][O:42][C:39]1[CH:38]=[CH:37][C:36]([CH2:35][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:45][CH:44]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH:32]([OH:34])[CH3:33])[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=3)[N:10]=2)=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 22959485VertellusHCID 666002411-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-YL)ethanone

Product 1

HCID 666112271-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanolYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 150 mL round-bottomed flask was added 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanone (1 g, 1.640 mmol) and sodium borohydrate (0.06 g, 1.640 mmol) in DCM (10 mL)-MeOH (10 mL). The suspension was stirred at room temperature for 16 h. The solution was quenched by saturated NH4Cl, extracted the aqueous with DCM (3×), the combined organic was dried over MgSO4, concentrated in vacuum to provide 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol (0.9 g, 90% yield) as a yellow solid. m/z (ESI positive ion) m/z: 612 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.36 (d, J=6.46 Hz, 3H) 2.57 (s, 3H) 3.74 (s, 3H) 3.91 (s, 3H) 4.75 (dd, J=6.26, 4.50 Hz, 1H) 4.83 (d, J=12.32 Hz, 4H) 5.25 (d, J=4.30 Hz, 1H) 6.82-6.97 (m, 4H) 7.19-7.35 (m, 4H) 7.98-8.14 (m, 2H) 8.30 (d, J=2.35 Hz, 1H) 8.78 (d, J=2.35 Hz, 1H) 11.68 (s, 1H).

Workup

  1. customThe solution was quenched by saturated NH4Cl
  2. extractionextracted the aqueous with DCM (3×)
  3. dry with materialthe combined organic was dried over MgSO4
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-a51ac4794438444e90e57483417ef4ca
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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