Sodium Carbonate → HCID 58541985, compound

HRID 1966733Notes

Reaction equation

HRID 1966733 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]2[N:6]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:16]=[N:17][NH:18][N:19]=3)=[N:8][C:4]=2[CH:3]=1.[NH2:26][C:27]1[N:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=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>[C:20]([N:6]1[C:5]2[CH:24]=[CH:25][C:2]([C:30]3[CH:29]=[N:28][C:27]([NH2:26])=[N:32][CH:31]=3)=[CH:3][C:4]=2[N:8]=[C:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]=[N:17][NH:18][N:19]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 58541950HCID 58541950, compound

Product 1

HCID 58541985HCID 58541985, compoundYield 8.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a sealed vial is added 5-bromo-1-tert-butyl-2-[2-(2H-tetrazol-5-yl)-phenyl]-1H-benzimidazole (190 mg, 0.478 mmol) in DMF (5 mL), followed by the addition of 2-aminopyrimidine-5-boronic acid pinacol ester (126 mg, 0.57 mmol), tetrakis(triphenylphosphine)palladium(0) (55 mg, 0.048 mmol) and 2M aq. Na2CO3 (1 mL, 2 mmol). The reaction mixture is heated under Argon at 110° C. for 3 hours. The residue is diluted with EtOAc, washed with brine, dried with Na2SO4, filtered and concentrated. The residue is loaded onto a silica gel column. The column is eluted with 0-20% 7M NH3 in MeOH/CH2Cl2. The product fractions are collected and concentrated to afford the title compound (16 mg, 8%) as a light yellow solid. LCMS (ESMS): m/z 412.67 (M++1)

Workup

  1. washwashed with brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe column is eluted with 0-20% 7M NH3 in MeOH/CH2Cl2
  6. customThe product fractions are collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ceabf347d1a54e13a8ef81363dd33d66
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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