Ethylene Glycol → HCID 69080407, compound

HRID 1926882Notes

Reaction equation

HRID 1926882 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].Cl[C:8]1[C:9]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[C:15]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:14][C:10]=2[N:11]=[CH:12][N:13]=1>CN(C=O)C.O>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]2[C:9]3[C:8]([O:5][CH2:4][CH2:3][OH:6])=[N:13][CH:12]=[N:11][C:10]=3[O:14][C:15]=2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 69080407HCID 69080407, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add, at 0° C., 59 mg (1.5 mmol) of 60% sodium hydride to a solution of 461 mg (7.4 mmol) ethylene glycol in 10 ml DMF. After warming to room temperature, continue stirring for 1 h. Then add 0.50 g (1.5 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and stir the mixture for 3 h at room temperature. Next, dilute with water and extract with ethyl acetate. Wash the organic phase with saturated sodium chloride solution, dry over magnesium sulphate and concentrate by evaporation. The raw product thus obtained is purified by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile). In this way, 412 mg (77% of theor.) 2-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}ethanol is obtained.

Workup

  1. additionAdd, at 0° C.
  2. stirringstir the mixture for 3 h at room temperature
  3. extractionextract with ethyl acetate
  4. washWash the organic phase with saturated sodium chloride solution
  5. dry with materialdry over magnesium sulphate
  6. concentrationconcentrate by evaporation
  7. customThe raw product thus obtained
  8. customis purified by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile)

Sources & evidence

ORD record
ord-94155a9a4c3d4d56b007972bfcc7ad93
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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