Acetic Acid → 2-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-(benzylamino)imidazo[4,5-b]pyridine

HRID 2181420Notes

Reaction equation

HRID 2181420 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13](Cl)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CC([O-])(C)C.[Na+].CC(O)=O>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13]([NH:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 224861525-Chloro-2-(4-fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)imidazo[4,5-b]pyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 98912922-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-(benzylamino)imidazo[4,5-b]pyridineYield 50%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
160 °C

Procedure

2-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-(chloro)imidazo[4,5-b]pyridine (100 mg; 0.25 mmol), R-(+)-BINAP (10 mg; 0.016 mmol), Pd2(dba)3 (22 mg; 0.024 mmol) are suspended in xylene (16 ml), benzylamine (0.53 ml; 4.9 mmol) is added, followed by NaOtBu (47 mg; 0.49 mmol) and heated to 160° C. for 10 min. under argon. The reaction mixture is poured on water (100 ml) containing HOAc (2 ml) and extracted with TBME three times. The combined organic phases are washed with 2N Na2CO3, dried over Na2SO4 and evaporated to dryness. Purification via SiO2 chromatography (TBME/hexane 6:4 to 10:0) and recrystalisation from TBME yields the title compound as colorless crystals (50 mg. 50%).

Workup

  1. additionThe reaction mixture is poured on water (100 ml)
  2. extractionextracted with TBME three times
  3. washThe combined organic phases are washed with 2N Na2CO3
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customPurification
  7. customvia SiO2 chromatography (TBME/hexane 6:4 to 10:0) and recrystalisation from TBME

Sources & evidence

ORD record
ord-2ab1606ce7f9427aa6d580b640dc68d6
Source dataset
uspto-grants-2005_05
Patent number
US06891039B2

Reaction notes

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