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

HRID 1812120Notes

Reaction equation

HRID 1812120 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:24][C:25]4[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)=[N:18][CH:19]=[C:20]([CH:23]=3)[CH:21]=[O:22])[N:10]=2)=[CH:5][CH:4]=1.ClCCl.CO.[BH4-].[Na+].[NH4+].[Cl-]>O>[CH3:41][O:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:43][CH:42]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:23]=[C:20]([CH2:21][OH:22])[CH:19]=[N:18][C:17]=3[NH:24][C:25]3[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[N:10]=2)=[CH:39][CH:38]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 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 84.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (1.0 g, 1.731 mmol) in dichloromethane (20 mL, 306 mmol) and methanol (20 mL, 494 mmol) was stirred at 0° C. and treated in portions with sodium borohydride powder (Aldrich) (0.211 g, 5.57 mmol). The resulting suspension was warmed up to room temperature and stirred for 1 h. The reaction mixture was treated with saturated NH4Cl (10 mL), diluted with water (40 mL) and stirred at room temperature for 2 h. The reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give (5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methanol (0.850 g, 1.466 mmol, 85yield). m/z (ESI, +ve ion) 580.2 (M+H)+.

Workup

  1. temperatureThe resulting suspension was warmed up to room temperature
  2. stirringstirred for 1 h
  3. stirringstirred at room temperature for 2 h
  4. extractionextracted with dichloromethane (3×50 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94979845eb9c4b649e04d401d5f2ff14
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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