Triethylamine → 3-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)benzyl methanesulfonate

HRID 2067904Notes

Reaction equation

HRID 2067904 reaction equation
[F:1][CH:2]([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[C:19]([CH2:23][OH:24])[CH:20]=[CH:21][CH:22]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl.O>[CH3:33][S:34]([O:24][CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([NH:16][C:13]2[N:12]=[CH:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH:2]([F:1])[F:25])=[CH:5][CH:6]=3)=[CH:15][N:14]=2)[CH:18]=1)(=[O:36])=[O:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68725684(3-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)methanol

Product 1

HCID 866601223-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)benzyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)methanol 36 (6.22 mmol) in DCM (30 mL) is added triethylamine (9.33 mmol) and methanesulfonyl chloride (7.47 mmol). The reaction mixture is stirred at rt for 1.5 h. The reaction is diluted with H2O (10 mL) and washed with Na2CO3 solution (3×20 mL). The organic layer is washed with brine, dried over MgSO4 and concentrated to afford 3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)benzyl methanesulfonate 37. MS (m/z) (M+1)+422.1.

Workup

  1. washwashed with Na2CO3 solution (3×20 mL)
  2. washThe organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cab46a8316724de298dbce131e4e10a4
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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