Cesium carbonate → HCID 49858287, compound

HRID 1260548Notes

Reaction equation

HRID 1260548 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.[Cu](Br)Br>[CH:9]([O:8][C:5]1[N:4]=[CH:3][C:2]([O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:17][CH:18]=2)=[CH:7][N:6]=1)([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 142426565-Bromo-2-[(propan-2-yl)oxy]pyrimidineHCID 59956161N-[3-(4-Hydroxyphenyl)-1-methylpropyl]acetamide

Product 1

HCID 49858287HCID 49858287, compound

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-Bromo-2-isopropoxypyrimidine (100 mg, 0.46 mmol), N-[3-(4-hydroxyphenyl)-1-methylpropyl]acetamide (95 mg, 0.46 mmol), cesium carbonate (180 mg, 0.552 mmol), copper bromide (66 mg, 0.46 mmol) were stirred in 5 ml of NMP at 160° C. under argon for 5 h. Following addition of equimolar amounts of the components stirring was continued at 160° C. for a further 3 h. The batch was filtered, the filtrate was concentrated and admixed with ethyl acetate and water, and the organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 3 mg (1%), M+H+: 344.23.

Workup

  1. additionaddition of equimolar amounts of the components
  2. filtrationThe batch was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe organic phase was separated off
  5. concentrationconcentrated
  6. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-794dc82d5b3f4989b5392752eea4f316
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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