2-(Dimethylamino)ethanol → HCID 59244751, compound

HRID 912391Notes

Reaction equation

HRID 912391 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:6][CH2:7][OH:8])[CH3:5].Cl[C:10]1[CH:15]=[C:14]([N:16]2[C:20]3[N:21]=[C:22]([N:50]4[CH2:55][CH2:54][O:53][CH2:52][CH2:51]4)[N:23]=[C:24]([C:25]4[CH:26]=[N:27][C:28]([N:31]([CH2:41][C:42]5[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=5)[CH2:32][C:33]5[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=5)=[N:29][CH:30]=4)[C:19]=3[CH2:18][CH2:17]2)[CH:13]=[CH:12][N:11]=1>C1(C)C=CC=CC=1>[CH3:3][N:4]([CH3:5])[CH2:6][CH2:7][O:8][C:12]1[CH:13]=[C:14]([N:16]2[C:20]3[N:21]=[C:22]([N:50]4[CH2:51][CH2:52][O:53][CH2:54][CH2:55]4)[N:23]=[C:24]([C:25]4[CH:30]=[N:29][C:28]([N:31]([CH2:32][C:33]5[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=5)[CH2:41][C:42]5[CH:43]=[CH:44][C:45]([O:48][CH3:49])=[CH:46][CH:47]=5)=[N:27][CH:26]=4)[C:19]=3[CH2:18][CH2:17]2)[CH:15]=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 45258863HCID 45258863, compound

Product 1

HCID 59244751HCID 59244751, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (15 mg, 60% mineral oil dispersion, 5 equivalents) and N,N-dimethylaminoethanol (39 μl, 5 equivalents) were added to toluene (1.3 ml). After refluxing for 5 minutes, stirring was carried out at 50° C. for 15 minutes. {5-[7-(2-Chloro-pyridin-4-yl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl}-bis-(4-methoxy-benzyl)-amine (50 mg) obtained in Step A in Example 1-H-31 was added, followed by refluxing overnight, and the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=30/1 to 10/1), to obtain a colorless solid (54 mg, 100%).

Workup

  1. temperatureAfter refluxing for 5 minutes
  2. temperatureby refluxing overnight
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=30/1 to 10/1)

Sources & evidence

ORD record
ord-b1c172961a5e4af3ae15b00344184ad0
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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