1,4-Dioxane → HCID 67295403, compound

HRID 629017Notes

Reaction equation

HRID 629017 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([S:14][CH3:15])=[CH:4][N:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+].O1CCOCC1>CC(=O)OCC.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.O>[CH3:15][S:14][C:5]1[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:7][C:2]([C:20]2[CH:21]=[CH:22][C:17]([NH2:16])=[CH:18][CH:19]=2)=[N:3][CH:4]=1

Participants

8

Reactant 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86673505HCID 86673505, compound

Product 1

HCID 67295403HCID 67295403, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2-chloro-5-(methylthio)pyrimidin-4-yl)morpholine (0.3 g, 1.22 mmole), 4-aminophenylboronic acid pinacol ester (0.58 g, 2.68 mmole), sodium bicarbonate (0.28 g, 2.68 mmole), Pd(PPh3)4 (0.14 g, 0.122 mmole), dioxane (15 ml) and H2O (3.5 ml) was heated to reflux. After 12 hrs, the reaction mixture was cooled, diluted with EA, washed with brine, and dried (MgSO4), and the solvent was removed in vacuo. Purification on silica gel (EA/Hex=1/2) yielded the desired compound (180 mg, 49%).

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe reaction mixture was cooled
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customPurification on silica gel (EA/Hex=1/2)

Sources & evidence

ORD record
ord-395b9f37c586456b81e14638587e397a
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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