1,2-Dimethoxyethane → 4-[4-(Methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine-2-yl]aniline

HRID 2353641Notes

Reaction equation

HRID 2353641 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:3]=1.COCCOC.CC1(C)C(C)(C)OB([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O.C(O)C>[CH3:12][S:9]([CH2:8][C:6]1[CH:5]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:3]=[C:2]([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[N:7]=1)(=[O:11])=[O:10]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59379935HCID 59379935, compound

Product 1

HCID 593800394-[4-(Methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine-2-yl]anilineYield 26.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-4-(methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine (5 g, 17.1 mmol), was dissolved in a mixture of DMF:DME:water:ethanol (16.5 mL:41 mL:18 mL:12 mL). 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.62 g, 25.6 mmol), a 2M aqueous solution of sodium carbonate (25 mL), and dichlorobis(triphenylphosphine) palladium (600 mg) were added and the mixture refluxed for 5 hours under a nitrogen atmosphere. The mixture was cooled, diluted with water and extracted into DCM. The organic layer was dried over Na2SO4, filtered and evaporated. The crude material was dissolved in minimum of hot DCM then hexane added and the precipitate filtered to give the desired material (1.6 g).

Workup

  1. temperaturethe mixture refluxed for 5 hours under a nitrogen atmosphere
  2. temperatureThe mixture was cooled
  3. extractionextracted into DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe crude material was dissolved in minimum of hot DCM
  8. additionhexane added
  9. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-d7f47d828d6c41d4acf972a5e83555f0
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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