Dimethyl Ether → HCID 60204557, compound

HRID 507655Notes

Reaction equation

HRID 507655 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[C:12]([CH3:13])=[CH:11][N:10]=[C:9]([NH:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][NH:19][C:18]3=[O:22])[N:8]=2)=[CH:4][CH:3]=1.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].COC>ClCCl.CO.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>[CH3:13][C:12]1[C:7]([C:5]2[S:6][C:2]([C:24]3[S:23][CH:27]=[CH:26][CH:25]=3)=[CH:3][CH:4]=2)=[N:8][C:9]([NH:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][NH:19][C:18]2=[O:22])=[N:10][CH:11]=1

Participants

8

Reactant 4

HCID 8254Dimethyl EtherHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 60204554HCID 60204554, compound

Product 1

HCID 60204557HCID 60204557, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
145 °C

Procedure

1-(2-(4-(5-Bromothiophen-2-yl)-5-methylpyrimidin-2-ylamino)ethyl)imidazolidin-2-one (0.1 g, 0.26 mmol), thiophen-2-ylboronic acid (0.066 g, 0.52 mmol), and sodium carbonate (0.26 mL of 2 M solution, 0.52 mmol) were added to a microwave tube containing dimethyl ether (2 mL). The tube was flushed with nitrogen and tetrakis(triphenylphosphine)palladium (0.06 g, 0.054 mmol) was added. The tube was capped and heated to 145° C. for 20 min in a Personal Chemistry microwave. The reaction was diluted with a mixture of 2:1 dichloromethane and methanol (9 mL), filtered through a pad of celite, washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was dried with sodium sulfate, concentrated in vacuo and purified by flash chromatography on silica gel using a gradient 2 to 10% of methanol in dichloromethane to afford a yellow solid. Yield=0.036 g. MS (M+H)+ 386.

Workup

  1. additionwas added
  2. customThe tube was capped
  3. filtrationfiltered through a pad of celite
  4. washwashed with saturated aqueous sodium bicarbonate, water and brine
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel using a gradient 2 to 10% of methanol in dichloromethane
  8. customto afford a yellow solid

Sources & evidence

ORD record
ord-9425f53fcbe24b97b7b4c2e07f6322f0
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

Loading…