Sodium Carbonate → HCID 58016808, compound

HRID 1926921Notes

Reaction equation

HRID 1926921 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:17](Br)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CS(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:17]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58016896HCID 58016896, compound

Product 1

HCID 58016808HCID 58016808, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Stir 55 mg (0.131 mmol) 6-[(6-bromo-5-phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoic acid methyl ester, 0.131 ml of 2 M aqueous sodium carbonate solution (0.26 mmol), 4.6 mg (0.006 mmol) bis(triphenylphosphine)palladium(II) chloride and 20 mg (0.164 mmol) phenylboronic acid under argon in 0.4 ml DMSO for 1 h at 80° C. After cooling, purify the mixture directly by preparative RP-HPLC (gradient: water/acetonitrile). 35 mg (64.1% of theor.) of the target compound is obtained.

Workup

  1. temperatureAfter cooling
  2. custompurify the mixture directly by preparative RP-HPLC (gradient: water/acetonitrile)
  3. custom35 mg (64.1% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-6f3125d33244489d9068b47338287237
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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