Hydrochloric Acid → HCID 9809953, compound

HRID 1599020Notes

Reaction equation

HRID 1599020 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[C:19]([O:26][CH2:27][CH2:28][OH:29])[N:18]=[C:17]([C:30]3[N:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:38][C:39]1[CH:40]=[N:41][C:42](Cl)=[N:43][CH:44]=1.Cl>O1CCCC1.CC(N(C)C)=O>[Br:38][C:39]1[CH:40]=[N:41][C:42]([O:29][CH2:28][CH2:27][O:26][C:19]2[N:18]=[C:17]([C:30]3[N:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[N:16]=[C:15]([NH:14][S:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=3)(=[O:12])=[O:13])[C:20]=2[C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[N:43][CH:44]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidineHCID 18931081HCID 18931081, compound

Product 1

HCID 9809953HCID 9809953, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-tert-butyl-N-{6-(2-hydroxyethoxy)-5-(2-thienyl)-2-(2-pyrimidinyl)-pyrimidin-4-yl}benzenesulfonamide (1790 mg) in tetrahydrofuran (20 ml) is added sodium hydride (60% dispersion, 413 mg) at room temperature, and thereto is added dimethylacetamide (4 ml), and the mixture is stirred for 20 minutes. To the reaction mixture is added 5-bromo-2-chloro-pyrimidine (952 mg), and the mixture is stirred at room temperature for 46 hours. The mixture is acidified with 10% hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=4:1) to give the title compound (617 mg) as a crystal.

Workup

  1. stirringthe mixture is stirred at room temperature for 46 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer is washed
  4. customdried
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=4:1)

Sources & evidence

ORD record
ord-acc1c84b2cce4b4cbfbbd693d09e943f
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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