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

HRID 1621646Notes

Reaction equation

HRID 1621646 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:45]=[CH:44][C:8]([CH2:9][N:10]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)[C:11]2[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([C:18]3[C:19]([NH:26][C:27]4[CH:28]=[N:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=4)=[N:20][CH:21]=[C:22]([CH:25]=3)[CH:23]=[O:24])[N:12]=2)=[CH:7][CH:6]=1.[Cl-].[NH4+].O>CO.C(Cl)Cl>[CH3:43][O:42][C:39]1[CH:38]=[CH:37][C:36]([CH2:35][N:10]([CH2:9][C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:45][CH:44]=2)[C:11]2[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([C:18]3[CH:25]=[C:22]([CH2:23][OH:24])[CH:21]=[N:20][C:19]=3[NH:26][C:27]3[CH:28]=[N:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)[N:12]=2)=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 59548440(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methanolYield 96.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (103 mg, 2.72 mmol) was added to a suspension of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (Example 144, step 1) (522.8 mg, 0.905 mmol) in a mixture of methanol (5.0 mL) and DCM (5.0 mL) at 0° C. The resulting solution was stirred at 0° C. for 5 min and then was allowed to warm to 25° C. and stir for 45 min. Saturated aqueous ammonium chloride (10 mL) and water (20 mL) were subsequently added, and the resulting mixture was extracted with DCM (2×50 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide (5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methanol (504.5 mg, 0.870 mmol, 96% yield) as a yellow-orange solid. m/z (ESI, +ve ion) 580.2 (M+H)+.

Workup

  1. temperatureto warm to 25° C.
  2. stirringstir for 45 min
  3. extractionthe resulting mixture was extracted with DCM (2×50 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b76c12f3cda046b38bc3a69eb3ddaeb3
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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