Acetic Acid → HCID 18545645, compound

HRID 1267080Notes

Reaction equation

HRID 1267080 reaction equation
C(OC([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]4[CH:31]=[C:30]([Cl:32])[C:29]([Cl:33])=[C:28]([Cl:34])[CH:27]=4)[N:20]=3)=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=O)C=C.C(O)(=O)C.C([SnH](CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>ClCCl.CN(C=O)C>[Cl:32][C:30]1[CH:31]=[C:26]([NH:25][C:21]2[N:20]=[C:19]([C:16]3[CH:17]=[CH:18][C:13]([N:10]4[CH2:11][CH2:12][NH:7][CH2:8][CH2:9]4)=[N:14][CH:15]=3)[CH:24]=[CH:23][N:22]=2)[CH:27]=[C:28]([Cl:34])[C:29]=1[Cl:33]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5948TributylstannaneHCID 516892Sodium BicarbonateHCID 18545608HCID 18545608, compound

Product 1

HCID 18545645HCID 18545645, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-(4-allyloxycarbonylpiperazin-1-yl)pyridin-5-yl)-N-(3,4,5-trichlorophenyl)-2-pyrimidineamine (170 mg,0.33 mmol) in dichloromethane and DMF (3 ml,1:1 mixture) was stirred with acetic acid (1 ml), dichloro-bis(triphenylphosphine)palladium (II) (15 mg) and tri-n-butyltin hydride at room temperature for 5 min. The reaction was added to a saturated aqueous NaHCO3 solution, which was extracted with ethyl acetate. The organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was triturated with hexane and then subjected to column chromatography (silica gel with 1% ammonium hydroxide-8% methanol-dichloromethane) to give the title compound (60 mg) as an off-white solid m.p. 208-211°. δH(d6 DMSO) 10.03(1H, s), 8.91 (1H, d, J 2.5 Hz), 8.51 (1H, d, J 5.4 Hz), 8.22 (1H, dd, J 9.1, 2.5 Hz),8.16 (2H, s), 7.43 (1H, d, J 5.4 Hz), 3.56 (4H, m) and 2.78 (4H, m).

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-eff3941123d248a181a249cddbe2964c
Source dataset
uspto-grants-2003_04
Patent number
US06552029B1

Reaction notes

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