Sodium Carbonate → HCID 53237837, compound

HRID 1966790Notes

Reaction equation

HRID 1966790 reaction equation
Br[C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:7]([C:9]3[CH:10]=[C:11]([CH2:20][OH:21])[CH:12]=[CH:13][C:14]=3[N:15]3[CH:19]=[N:18][CH:17]=[N:16]3)=[N:8][C:4]=2[CH:3]=1.[NH2:28][C:29]1[N:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=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>[NH2:28][C:29]1[N:34]=[CH:33][C:32]([C:2]2[CH:27]=[CH:26][C:5]3[N:6]([C:22]([CH3:23])([CH3:25])[CH3:24])[C:7]([C:9]4[CH:10]=[C:11]([CH2:20][OH:21])[CH:12]=[CH:13][C:14]=4[N:15]4[CH:19]=[N:18][CH:17]=[N:16]4)=[N:8][C:4]=3[CH:3]=2)=[CH:31][N:30]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 58542017HCID 58542017, compound

Product 1

HCID 53237837HCID 53237837, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a sealed vial is added [3-(5-bromo-1-tert-butyl-1H-benzoimidazol-2-yl)-4-[1,2,4]triazol-1-yl-phenyl]methanol (47 mg, 0.11 mmol) in DMF (2 mL), followed by the addition of 2-aminopyrimidine-5-boronic acid pinacol ester (29 mg, 0.13 mmol) and tetrakis(triphenylphosphine)palladium(0) (13 mg, 0.011 mmol) and 2M aqueous Na2CO3 (0.25 mL, 0.5 mmol). The reaction mixture is heated under argon at 110° C. for 2 hours. The residue is diluted with EtOAc (10 mL), washed with brine (10 mL), and dried under anhydrous Na2SO4 (500 mg). The mixture is filtered and is concentrated. The residue is purified by silica gel flash chromatography with 0-10% 2M NH3 in MeOH/CH2Cl2 as the eluent. The product fractions are collected and concentrated to afford the title compound (30 mg, 62%). LCMS (ESMS): m/z 441.32 (M++1)

Workup

  1. washwashed with brine (10 mL)
  2. customdried under anhydrous Na2SO4 (500 mg)
  3. filtrationThe mixture is filtered
  4. concentrationis concentrated
  5. customThe residue is purified by silica gel flash chromatography with 0-10% 2M NH3 in MeOH/CH2Cl2 as the eluent
  6. customThe product fractions are collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c0a8735efa004ca5bb4f180cc601a7f9
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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