HCID 70123251, compound → 2-[1-(4-(Tert-butyloxycarbonyl)-piperazine-2-yl)-ethylamino]-4-(benzimidazol-1-yl)-pyrimidine

HRID 429288Notes

Reaction equation

HRID 429288 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[CH:24]([NH:26][C:27]1[N:32]=[C:31]([N:33]2[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[N:35]=[CH:34]2)[C:30](Br)=[CH:29][N:28]=1)[CH3:25])=O)C1C=CC=CC=1>CC(O)C.[OH-].[OH-].[Pd+2]>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][NH:11][CH:12]([CH:24]([NH:26][C:27]2[N:32]=[C:31]([N:33]3[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=4[N:35]=[CH:34]3)[CH:30]=[CH:29][N:28]=2)[CH3:25])[CH2:13]1)=[O:18])([CH3:21])([CH3:22])[CH3:23]

Participants

4

Reactant 1

HCID 70123251HCID 70123251, compound

Product 1

HCID 702154342-[1-(4-(Tert-butyloxycarbonyl)-piperazine-2-yl)-ethylamino]-4-(benzimidazol-1-yl)-pyrimidineYield 30.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 2-[1-(1-(benzyloxycarbonyl)-4-(tert-butyloxycarbonyl)-piperazin-2-yl)-ethylamino]-4-(benzimidazol-1-yl)-5-bromopyrimidine (83 mg) in 1 mL of iPrOH was stirred over Pd(OH)2/C (75 mg) under an H2 atmosphere (balloon) for 2 days, then filtered through Celite®, washing liberally with MeOH, and concentrated. The residue was dissolved in 10 mL of 0.2 N HCl and washed with 2×5 mL of CH2Cl2. The aqueous phase was basified (pH>1 1) with 1N NaOH and extracted with 4×10 mL of EtOAc. The combined organics were dried over Na2SO4 and concentrated, and the residue was purified by preparative thin-layer chromatography, eluting with 9:1 CH2Cl2—MeOH to provide 17 mg of the title compound. Mass spectrum (ESI) 368.3 (M−tBu).

Workup

  1. filtrationfiltered through Celite®
  2. washwashing liberally with MeOH
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 10 mL of 0.2 N HCl
  5. washwashed with 2×5 mL of CH2Cl2
  6. extractionextracted with 4×10 mL of EtOAc
  7. dry with materialThe combined organics were dried over Na2SO4
  8. concentrationconcentrated
  9. customthe residue was purified by preparative thin-layer chromatography
  10. washeluting with 9:1 CH2Cl2—MeOH

Sources & evidence

ORD record
ord-4ffbd4712c304644b35b2d425764481b
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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