Triethylamine → 4-(5-Bromopyrimidin-2-ylamino)phenethyl methanesulfonate

HRID 2067870Notes

Reaction equation

HRID 2067870 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl.O>[CH3:25][S:26]([O:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[CH:14][CH:13]=1)(=[O:28])=[O:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576326232-(4-(5-Bromopyrimidin-2-ylamino)phenyl)ethanol

Product 1

HCID 866601174-(5-Bromopyrimidin-2-ylamino)phenethyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(5-bromopyrimidin-2-ylamino)phenyl)ethanol 18 (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 (3×10 mL). The organic layer is washed with brine, dried over MgSO4 and concentrated to afford 4-(5-bromopyrimidin-2-ylamino)phenethyl methanesulfonate 19. 1H NMR (400 MHz, CD2Cl2) δ 8.36 (s, 2H), 7.65 (bs, 1H), 7.49 (d, J=8.8 Hz, 2H), 7.14 (d, J=8.4 Hz, 2H), 4.31 (t, J=6.8 Hz, 2H), 2.95 (t, J=6.8 Hz, 2H), 2.79 (s, 3H). MS (m/z) (M+1)+: 372.0, 374.0.

Workup

  1. washwashed with Na2CO3 solution (3×10 mL)
  2. washThe organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8561608a6a57408f8c6366f996162d0d
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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