Sodium borohydride → 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 1812209Notes

Reaction equation

HRID 1812209 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.[BH4-].[Na+]>C1COCC1>[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

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 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)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 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 (0.1350 g, 0.221 mmol) in THF (5.00 mL) was treated with sodium borohydride (0.042 g, 1.107 mmol) at 0° C. and the resulting mixture was stirred for 10 min before being allowed to warm to room temperature for 1 h. The resulting suspension was quenched with 1 N aqueous NaOH, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were then washed with brine, dried over Na2SO4, and concentrated to give 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, which was used directly without further purification.

Workup

  1. customThe resulting suspension was quenched with 1 N aqueous NaOH
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. washThe combined organic layers were then washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2233fd56095d4c2ab0d654b79da471ba
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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