Potassium Iodide → HCID 58280104, compound

HRID 2189116Notes

Reaction equation

HRID 2189116 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([O:18][CH2:19][CH:20]4[CH2:24][CH2:23][CH2:22][NH:21]4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[I-].[K+].[CH3:42][O:43][C:44](=[O:49])[CH2:45][CH2:46][CH2:47]Br>C1COCC1.O>[CH3:42][O:43][C:44](=[O:49])[CH2:45][CH2:46][CH2:47][N:21]1[CH2:22][CH2:23][CH2:24][CH:20]1[CH2:19][O:18][C:16]1[C:17]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[C:10]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:11][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 107604Methyl 4-bromobutyrateHCID 58280184HCID 58280184, compound

Product 1

HCID 58280104HCID 58280104, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 100 mg (0.25 mmol) of (+/−)-5-(4-methoxyphenyl)-6-phenyl-4-(pyrrolidin-2-ylmethoxy)furo[2,3-d]-pyrimidine (Example 38A) in 2 ml of THF and successively add 65 μl (0.374 mmol) of DIEA, 4.1 mg (0.025 mmol) of potassium iodide and 45 mg (0.25 mmol) of 4-bromobutyric acid methyl ester. Heat the mixture under reflux for 1 h and then add to water with cooling. Extract three times with ethyl acetate and wash the combined organic phases twice with buffer solution (pH 7) and with saturated sodium chloride solution. Dry the solution over magnesium sulphate and concentrate under reduced pressure. Purify the crude product by preparative RP-HPLC (eluent: acetonitrile/water gradient). 47 mg (37.6% of theory) of the target product are obtained.

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 1 h
  3. temperaturewith cooling
  4. extractionExtract three times with ethyl acetate
  5. washwash the combined organic phases twice with buffer solution (pH 7)
  6. dry with materialDry the solution over magnesium sulphate
  7. concentrationconcentrate under reduced pressure
  8. customPurify the crude product by preparative RP-HPLC (eluent: acetonitrile/water gradient)
  9. custom47 mg (37.6% of theory) of the target product are obtained

Sources & evidence

ORD record
ord-02949933d0ec41fcb3f26b3d27b5f4de
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

Loading…