Water → HCID 9886756, compound

HRID 2300812Notes

Reaction equation

HRID 2300812 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23](I)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.C(O)CC>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 59924653HCID 59924653, compound

Product 1

HCID 9886756HCID 9886756, compoundYield 36.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 27 mg of 2-[(S)-1-phenylethylamino]-4-[5-iodobenzimidazol-1-yl]pyrimidine, 22 mg phenyl boronic acid, 42 mg potasium carbonate, 0.7 mg Pd(PPh3)4, 1.5 mL of H2O and 1.5 mL n-propanol was refluxed under nitrogen for 2 hours. The solution was cooled to room temperature, added to 100 mL of ethyl acetate and washed with saturated NaHCO3 and brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by MPLC eluting with methanol in methylene chloride to give 8.7 mg of the title compound. RF: 0.55 (5% MeOH in CH2Cl2). 1H NMR (300 MHz, 3:1 CD3OD/CDCl3): δ 1.62 (d, J=6.9 Hz, 3H), 5.17 (q, J=7.0 Hz, 1H), 1H), 7.05 (d, J=5.8 Hz, 1H), 7.2-7.65 (m, 12H), 7.89 (br s, 1H), 8.36 (br s, J=5.6 Hz, 1H), 8.8-8.95 (m, 1H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 392.3 (M+1).

Workup

  1. temperaturewas refluxed under nitrogen for 2 hours
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by MPLC
  7. washeluting with methanol in methylene chloride

Sources & evidence

ORD record
ord-e41e5a8c58de4fce95d38504c73f1342
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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