Sodium Carbonate → HCID 23291344, compound

HRID 365359Notes

Reaction equation

HRID 365359 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1B(O)O.[CH2:16]([O:23][CH2:24][C:25]1[N:30]=[CH:29][N:28]=[C:27]([O:31][CH2:32][CH2:33][CH3:34])[C:26]=1I)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO.C1(C)C=CC=CC=1.C(OCC)(=O)C.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>[CH2:16]([O:23][CH2:24][C:25]1[N:30]=[CH:29][N:28]=[C:27]([O:31][CH2:32][CH2:33][CH3:34])[C:26]=1[C:6]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[O:4][CH2:3][O:2][CH3:1])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 15402632Boronic acid, [4-methoxy-2-(methoxymethoxy)phenyl]-HCID 23291346HCID 23291346, compound

Product 1

HCID 23291344HCID 23291344, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methoxymethoxy-4-methoxyphenyl boronic acid (2.89 g, 13.65 mmol) in MeOH (8-10 ml) and 6-benzyloxymethyl-5-iodo-4-propoxy-pyrimidine (5 g, 13 mmol) in toluene (75 ml) was added an aqueous solution of 2 M sodium carbonate (14 ml) followed by Tetrakis(triphenylphosphine)palladium (0) (1.25 g, 1.08 mmol). The reaction was allowed to stir at 90-95° for 18 h. The mixture was cooled to room temperature then diluted with ethyl acetate, washed with water, sat'd NH4Cl, 5% NaHCO3 solution, brine and dried (MgSO4). After removing the solvent, flash chromatography of the residue (silica gel, 1:1 t-butyl methyl ether/hexane) provided the title compound as a solid (3.41 g, 62%).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customAfter removing the solvent, flash chromatography of the residue (silica gel, 1:1 t-butyl methyl ether/hexane)

Sources & evidence

ORD record
ord-9cef6f83e8904d7f9635a7b97a79aaec
Source dataset
uspto-grants-2000_10
Patent number
US06127371

Reaction notes

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