Water → HCID 9797110, compound

HRID 1977607Notes

Reaction equation

HRID 1977607 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[CH:10][N:9]=1.[H-].[Na+].Cl.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26]Cl.O>CN(C)C=O>[CH3:23][N:24]([CH2:25][CH2:26][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:11]=[CH:10][N:9]=1)[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 619210HCID 619210, compoundHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 9797110HCID 9797110, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-(2-hydroxyphenyl)-6-phenyl-pyrimidine (0.5 g, example 1) and sodium hydride (0.12 g, 80% in oil) in anhydrous dimethylformamide (5 ml) was stirred 20 minutes at room temperature. Then 2-dimethylaminoethyl chloride hydrochloride (0.29 g) was added and the solution was heated at 100° C. under stirring for 6 hours. The reaction mixture was cooled, then poured into water, and the separated oil was extracted with ethyl acetate. The organic layer was dried, then evaporated to dryness to give 500 mg of the title compound as a crude residue, which was purified through its hydrochloride salt. This was obtained by dissolving the free base in acetone, adding a hydrochloric acid ethereal solution and filtering off the crystallized salt.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe separated oil was extracted with ethyl acetate
  3. customThe organic layer was dried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-e602b794ad864aa7a18659316aa683ca
Source dataset
uspto-grants-2001_05
Patent number
US06235738B1

Reaction notes

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