Hydrochloric Acid → HCID 20703634, compound

HRID 429292Notes

Reaction equation

HRID 429292 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[CH:18]2)[CH:14]=[CH:13][N:12]=1)[CH3:9].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+].Cl>CS(C)=O.CCOC(C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:4][CH:3]1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[CH:18]2)[CH:14]=[CH:13][N:12]=1)[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 20703633HCID 20703633, compound

Product 1

HCID 20703634HCID 20703634, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[1-(1-methylpiperazine-2-yl)-ethylamino]-4-[benzimidazol-1-yl]-pyrimidine (EXAMPLE 20; 3 mg) in 4 mL of DMSO was added benzyl bromide (2 μL) and K2CO3 (2.2 mg). The mixture was stirred for 2d at room temperature, then diluted with 5 mL of EtOAc and poured into 10 mL of 1N HCl. The phases were separated and the aqueous phase was basified (pH>11) with 5N NaOH and extracted with 4×5 mL of EtOAc. The combined organics were dried over Na2SO4 and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2—MeOH to provide 1.9 mg of the title compound. Mass spectrum (ESI) 428.4 (M+1).

Workup

  1. customThe phases were separated
  2. extractionextracted with 4×5 mL of EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative thin-layer chromatography
  6. washeluting with 95:5 CH2Cl2—MeOH

Sources & evidence

ORD record
ord-44d96371fe3b450093f899504f0935ca
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

Loading…