Isopropyl iodide → HCID 68912207, compound

HRID 1517413Notes

Reaction equation

HRID 1517413 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH:22]2[C:27](=[O:36])[NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:44]([CH3:46])[CH3:45]>CC(C)=O>[NH2:1][C:2]1[N:3]=[C:4]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH:22]2[C:27](=[O:36])[NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:44]([CH3:46])[CH3:45])=[C:14]([O:19][CH3:20])[CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodide2×HCID 11430Potassium CarbonateHCID 135903251HCID 135903251, compound

Product 1

HCID 68912207HCID 68912207, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 2-amino-4-[(N-4-fluoro-phenyl-carbamoyl)-piperazin-1-yl]-6-(4-hydroxy-3-methoxy-phenyl)-pyrido[3,2-d]pyrimidine (96 μmole), anhydrous potassium carbonate (0.22 mmole) and 2-iodopropane (0.96 mmole) in acetone (7 ml) was refluxed under a nitrogen atmosphere for 20 hours. Then, another aliquot of 2-iodopropane was added and the reaction was continued for another 24 hours. Upon cooling, the reaction mixture was partitioned between ethyl acetate and brine and the aqueous layer was extracted several times with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. Purification of the crude residue by silica gel flash chromatography, using 10% methanol in CH2Cl2 as mobile phase, afforded the pure title compound (20 mg, yield 39%) which was characterized by its mass spectrum as follows: MS (m/z): 532 ([M+H]+, 100).

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 20 hours
  2. temperatureUpon cooling
  3. customthe reaction mixture was partitioned between ethyl acetate and brine
  4. extractionthe aqueous layer was extracted several times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customPurification of the crude residue by silica gel flash chromatography

Sources & evidence

ORD record
ord-c8e18f8d5ec844a993ce76a72f0dccd6
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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