Sodium Carbonate → HCID 68644254, compound

HRID 1158782Notes

Reaction equation

HRID 1158782 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:15]([OH:38])[CH2:16][N:17]([CH2:35][CH2:36]O)[C:18]([C:20]2[C:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:22][C:23]([N:26]([CH3:28])[CH3:27])=[N:24][CH:25]=2)=[O:19])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:27][N:26]([CH3:28])[C:23]1[N:22]=[C:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:20]([C:18]([N:17]2[CH2:35][CH2:36][O:38][CH:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=3)[CH2:16]2)=[O:19])=[CH:25][N:24]=1

Participants

3

Reactant 2

HCID 10340Sodium CarbonateHCID 86610923HCID 86610923, compound

Product 1

HCID 68644254HCID 68644254, compoundYield 14.6%

Conditions

Temperature
100 °C

Procedure

To 2-dimethylamino-4-phenylpyrimidin-5-carboxylic acid [2-(3-benzyloxyphenyl)-2-hydroxyethyl]-(2-hydroxyethyl)amide (0.20 g, 0.39 mmol) 48% hydrogen bromide solution (4 ml) is added. The mixture is heated at 100° C. for 1 hour, cooled to room temperature, poured onto water and neutralized (pH 7) with sodium carbonate solution. The precipitate is filtered oft washed with water and dried. The crude product is chromatographed on silicagel using chloroform and chloroform-ethyl acetate 9:1 mixture as eluent. 0.023 g light-yellow title compound is obtained, m.p.: 140° C.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate is filtered oft
  3. washwashed with water
  4. customdried
  5. customThe crude product is chromatographed on silicagel

Sources & evidence

ORD record
ord-d3badd827fa54996a8cd8fced8c8559d
Source dataset
uspto-grants-2010_10
Patent number
US07812031B2

Reaction notes

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