Sodium Carbonate → HCID 60204320, compound

HRID 2267309Notes

Reaction equation

HRID 2267309 reaction equation
[S:1]1[C:5]([C:6]2[C:11](Br)=[CH:10][N:9]=[C:8]([NH:13][CH2:14][CH2:15][N:16]3[C:20]([CH3:22])([CH3:21])[C:19](=[O:23])[NH:18][C:17]3=[O:24])[N:7]=2)=[CH:4][C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>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>[S:1]1[C:5]([C:6]2[C:11]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:10][N:9]=[C:8]([NH:13][CH2:14][CH2:15][N:16]3[C:20]([CH3:22])([CH3:21])[C:19](=[O:23])[NH:18][C:17]3=[O:24])[N:7]=2)=[CH:4][C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 60204257HCID 60204257, compound

Product 1

HCID 60204320HCID 60204320, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A 5 mL Personal Chemistry microwave tube was charged with 1-(2-(4-(benzo[b]thiophen-2-yl)-5-bromopyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (103 mg, 0.22 mmol), phenyl boronic acid (55 mg, 0.44 mmol), a 2 M aqueous solution of sodium carbonate (0.22 mL, 0.44 mmol), dioxane (2 mL) and tetrakis(triphenylphosphine)palladium (0) (52 mg, 0.044 mmol). The vessel was sealed and heated to 140° C. for 20 min with stirring. After cooling to r.t. the mixture was diluted with ethyl acetate (10 mL) and washed with a saturated aqueous solution of sodium hydrogen carbonate (10 mL). The organic layer was separated, dried over magnesium sulfate, filtered and the solvent evaporated in vacuo. The residue was purified by flash chromatography (chloroform/methanol 99:1 to 96:4 followed by a second column: ethyl acetate/hexane/methanol 50:48:2) to afford the title compound (17 mg, 17%). 1H NMR: δ (CDCl3, 400 MHz) 1.47 (s, 6 H), 3.60-3.68 (m, 2 H), 3.81-3.92 (m, 2 H), 6.32 (br. s., 1 H), 6.92 (s, 1 H), 7.26 (t, J=7 Hz, 1 H), 7.32 (t, J=7 Hz, 1 H), 7.36 (dd, J=3 Hz, 2 H), 7.44-7.47 (m, 3 H), 7.50 (d, J=8 Hz, 1 H), 7.79 (d, J=8 Hz, 1 H), 8.22 (s, 1 H): HRMS (M+H)+ Calcd. C25H23N5O2S 458.1650, found 458.1616

Workup

  1. customThe vessel was sealed
  2. temperatureAfter cooling to r.t. the mixture
  3. washwashed with a saturated aqueous solution of sodium hydrogen carbonate (10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customThe residue was purified by flash chromatography (chloroform/methanol 99:1 to 96:4

Sources & evidence

ORD record
ord-78e81bafeaa44f9ebbd1e571434ab6a0
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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