Water → HCID 58280058, compound

HRID 2189030Notes

Reaction equation

HRID 2189030 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][C:19]4[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=4)[O:22][CH2:23][C:24]([NH2:26])=O)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:5][CH:4]=1.N1C(Cl)=NC(Cl)=NC=1Cl.O.C(OCC)(=O)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:16]([NH:18][C:19]4[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=4)[O:22][CH2:23][C:24]#[N:26])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7954Cyanuric chlorideHCID 8857Ethyl AcetateHCID 58280134HCID 58280134, compound

Product 1

HCID 58280058HCID 58280058, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 800 mg (1.72 mmol) of 2-(3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxy)acetamide in 5 ml of DMF, cool to 0° C. and add 316 mg (1.72 mmol) of cyanuric chloride. Stir the mixture at 0° C. for 2 h. Then add water and ethyl acetate. After phase separation, extract the aqueous phase twice with ethyl acetate. Wash the combined organic phases three times with buffer solution (pH 7), dry them over magnesium sulphate and concentrate them under reduced pressure. The crude product is purified by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 20:1). 179 mg (22.3% of theory) of the target product are obtained as a white solid.

Workup

  1. customAfter phase separation
  2. extractionextract the aqueous phase twice with ethyl acetate
  3. washWash the combined organic phases three times with buffer solution (pH 7)
  4. dry with materialdry them over magnesium sulphate
  5. concentrationconcentrate them under reduced pressure
  6. customThe crude product is purified by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 20:1)
  7. custom179 mg (22.3% of theory) of the target product are obtained as a white solid

Sources & evidence

ORD record
ord-8fb2ea3389174c3f9912704e6dd54efa
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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