Ethylene Glycol → HCID 59749107, compound

HRID 747167Notes

Reaction equation

HRID 747167 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].F[C:8]1[CH:13]=[C:12]([C:14]2[C:15]([C:26]3[O:27][CH:28]=[CH:29][CH:30]=3)=[N:16][C:17]([NH2:25])=[N:18][C:19]=2[C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[CH:11]=[CH:10][N:9]=1>CN(C)C=O>[NH2:25][C:17]1[N:16]=[C:15]([C:26]2[O:27][CH:28]=[CH:29][CH:30]=2)[C:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([O:5][CH2:4][CH2:3][OH:6])[CH:13]=2)=[C:19]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[N:18]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 23020419HCID 23020419, compound

Product 1

HCID 59749107HCID 59749107, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In a reaction vessel, sodium hydride (15 mg, 0.372 mmol) was suspended in N,N-dimethylformamide (4 ml) and ethylene glycol (23 mg, 0.372 mmol) was added thereto, followed by stirring at 80° C. for 30 minutes under an atmosphere of nitrogen gas. Subsequently, 5-(2-fluoro-4-pyridyl)-4,6-di(2-furyl)-2-pyrimidinamine (100 mg, 0.310 mmol) was added thereto, followed by stirring for 14 hours under the same conditions. Then, the reaction was terminated by adding water thereto. The reaction mixture was extracted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and then the filtrate was concentrated. The resulting crude product was purified by silica gel column chromatography, to give the title compound (41 mg, 36%) as a pale yellow solid.

Workup

  1. stirringby stirring for 14 hours under the same conditions
  2. customThen, the reaction was terminated
  3. additionby adding water
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationthe filtrate was concentrated
  8. customThe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6fa12eaa1a034fd79be69d546e333631
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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