Water → HCID 59924931, compound

HRID 2300866Notes

Reaction equation

HRID 2300866 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]=[C:22](I)[CH:23]=[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)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].O>C(O)CC.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:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([C:34]5[C:35]6[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=6)[CH:31]=[CH:32][CH:33]=5)[CH:23]=[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

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 59924926HCID 59924926, compound

Product 1

HCID 59924931HCID 59924931, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 10311-PropanolSolvent

Procedure

2-[(S)-1-Phenylethylamino]-4-[6-iodobenzimidazol-1-yl]pyrimidine (EXAMPLE 415) (50 mg), 1-naphthyl boronic acid (22 mg), potassium carbonate (31 mg), and tetrakis(triphenylphosphine)palladium(0) (5 mg) were dissolved in degassed n-propanol (2.6 mL) and water (0.4 mL) and stirred at 80° C. under argon atmosphere for 15 hours. Upon cooling, the reaction mixture was filtered through Celite® (the ppt was washed with 10 mL of EtOAc) and evaporated. The residue was purified by preparative thin layer chromatoraphy eluted with 5% MeOH/CH2Cl2) giving 44 mg of the title compound. 1H NMR (500 MHz, CDCl3), δ 8.82 (br s, 1H), 8.38 (s, 1H), 7.97-7.75 (m, 4H), 7.54-7.29 (m, 9H), 7.19 (t, 1 H, J=7.5 Hz), 7.01 (d, 1H, J=Hz), 5.7 (s, 1H), 1.67 (d, 3H, J=7.0 Hz); Mass spectrum (ESI) 442.3 (M+1).

Workup

  1. temperatureUpon cooling
  2. filtrationthe reaction mixture was filtered through Celite® (the ppt
  3. washwas washed with 10 mL of EtOAc) and
  4. customevaporated
  5. customThe residue was purified by preparative thin layer chromatoraphy
  6. washeluted with 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0b4ca3a20ffc4f49bae88bafde1c7f15
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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