Triethylamine → HCID 86660115, compound

HRID 2067865Notes

Reaction equation

HRID 2067865 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][OH:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(Cl)Cl>[CH3:19][S:20]([O:16][CH2:15][CH2:14][O:13][C:12]1[CH:17]=[CH:18][C:9]([NH:8][C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[CH:10][CH:11]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68726270HCID 68726270, compound

Product 1

HCID 86660115HCID 86660115, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-(5-Bromopyrimidin-2-ylamino)phenoxy)ethanol 10 (26.6 mmol) is dissolved in DCM (50 mL) followed by addition of MsCl (32 mmol). The reaction vessel is chilled in an ice-water bath and triethylamine (53.3 mmol) is added slowly. The mixture is stirred at rt for 16 h. The solvent is removed and the residue is triturated with water (300 mL). The solid is filtered and dried under vacuum for 12 h to give 2-(4-(5-Bromopyrimidin-2-ylamino)phenoxy)ethyl methanesulfonate 11 as off-white solid. 1H NMR (400 MHz, d6-DMSO) δ 9.71 (s, 1H), 8.54 (s, 2H), 7.59 (d, J=9.2 Hz, 2H), 6.93 (d, J=9.2 Hz, 2H), 4.52 (m, 2H), 4.22 (m, 2H), 3.24 (s, 3H). MS (m/z) (M+1)+: 388.0, 340.0.

Workup

  1. temperatureThe reaction vessel is chilled in an ice-water bath
  2. customThe solvent is removed
  3. customthe residue is triturated with water (300 mL)
  4. filtrationThe solid is filtered
  5. customdried under vacuum for 12 h

Sources & evidence

ORD record
ord-a79264c27e3c4493aa946f29cbd37e4e
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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