Water → HCID 59380038, compound

HRID 2353627Notes

Reaction equation

HRID 2353627 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[N:3]=1.O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][C:23]=1[O:31][CH3:32].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.C(O)C>[CH3:32][O:31][C:23]1[CH:24]=[C:25]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]3[CH3:14])[CH:5]=[C:4]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[N:3]=2)[CH:26]=[CH:27][C:22]=1[NH2:21]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 57473274(4-Amino-3-methoxyphenyl)boronic acidHCID 575473562-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine

Product 1

HCID 59380038HCID 59380038, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine (700 mg, 2.29 mmol) was dissolved in a solution of 18% DMF in a mixture of 7:3:2 DME:water:ethanol (7 mL). (4-Amino-3-methoxy-phenyl)boronic acid (574 mg, 3.43 mmol), 2M sodium carbonate solution (4 mL) and dichlorobis(triphenylphosphine) palladium (81 mg) was then added to the solution and refluxed at 90° C. for 1 hour. The reaction was allowed to cool to room temp then partitioned between ethyl acetate (50 mL) and water (50 mL), the organics dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was dissolved in dichloromethane and filtered to remove insoluble material. The filtrates were purified using a companion.

Workup

  1. temperatureto cool to room temp
  2. customthen partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. dry with materialthe organics dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in dichloromethane
  7. filtrationfiltered
  8. customto remove insoluble material
  9. customThe filtrates were purified

Sources & evidence

ORD record
ord-869c9bfe74a445f79eac7fde64780dca
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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