Benzyl Bromide → HCID 86610921, compound

HRID 1158779Notes

Reaction equation

HRID 1158779 reaction equation
[OH:1][CH:2]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=1)[CH2:3][N:4]([CH3:24])[C:5]([C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)=[N:9][C:10]([N:13]([CH3:15])[CH3:14])=[N:11][CH:12]=1)=[O:6].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:32]([O:31][C:27]1[CH:26]=[C:25]([CH:2]([OH:1])[CH2:3][N:4]([CH3:24])[C:5]([C:7]2[C:8]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)=[N:9][C:10]([N:13]([CH3:14])[CH3:15])=[N:11][CH:12]=2)=[O:6])[CH:30]=[CH:29][CH:28]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 86610922HCID 86610922, compound

Product 1

HCID 86610921HCID 86610921, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 2-dimethylamino-4-(3,4-dichlorophenyl)pyrimidine-5-carboxylic acid [2-hydroxy-2-(3-hydroxyphenyl)ethyl]methylamide (0.92 g, 2 mmol), benzylbromide (1.71 g, 10 mmol), cesium carbonate (1.30 g, 4 mmol) and acetonitrile (25 ml) are boiled under stirring for 5 hours. The reaction mixture is evaporated in vacuum, dichloromethane (50 ml) is added to it, washed with water (3×50 ml), dried over sodium sulphate and evaporated. The residue is chromatographed on silicagel, using dichloromethane—methanol 100/1 mixture as eluent. 0.50 g (45.4%) of pale-yellow crystalline material is obtained, m.p.: 68-70° C.; [M+H]+ 551.

Workup

  1. customThe reaction mixture is evaporated in vacuum, dichloromethane (50 ml)
  2. additionis added to it
  3. washwashed with water (3×50 ml)
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue is chromatographed on silicagel

Sources & evidence

ORD record
ord-46c7f3bf15894670ad53f85cd67af775
Source dataset
uspto-grants-2010_10
Patent number
US07812031B2

Reaction notes

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