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

HRID 1812296Notes

Reaction equation

HRID 1812296 reaction equation
[CH3:1][Mg]Br.[CH3:4][O:5][C:6]1[CH:46]=[CH:45][C:9]([CH2:10][N:11]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[C:12]2[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([C:19]3[C:20]([NH:27][C:28]4[CH:29]=[N:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=4)=[N:21][CH:22]=[C:23]([CH:26]=3)[CH:24]=[O:25])[N:13]=2)=[CH:8][CH:7]=1.[Cl-].[NH4+].O>C1COCC1>[CH3:44][O:43][C:40]1[CH:39]=[CH:38][C:37]([CH2:36][N:11]([CH2:10][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH3:4])=[CH:46][CH:45]=2)[C:12]2[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([C:19]3[CH:26]=[C:23]([CH:24]([OH:25])[CH3:1])[CH:22]=[N:21][C:20]=3[NH:27][C:28]3[CH:29]=[N:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)[N:13]=2)=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 666113881-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanolYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylmagnesium bromide (1.4 M in 3:1 toluene/THF) (Aldrich, St. Louis, Mo.; 1.787 mL, 2.502 mmol) was added (dropwise, over 10 min) to a yellow-brown solution 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; 451.7 mg, 0.782 mmol) in THF (5.0 mL) at 0° C., and the resulting brown solution was stirred at 0° C. for 1 h. Saturated ammonium chloride (10 ml) and water (10 ml) were then added, THF was removed in vacuo, and the resulting mixture was extracted with EtOAc (2×60 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Trituration of the residue with hexanes (10 mL) furnished 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol (331.1 mg, 0.558 mmol, 71.3% yield) as a yellow-brown solid. m/z (ESI, +ve) 594.2 (M+H)+.

Workup

  1. customTHF was removed in vacuo
  2. extractionthe resulting mixture was extracted with EtOAc (2×60 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f46e7987aa24b26b3bc5ad9cb339052
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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