Triethylamine → HCID 86728316, compound

HRID 2171331Notes

Reaction equation

HRID 2171331 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])[CH:5]=[C:4]([Cl:14])[N:3]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:11][CH2:10][C:9]([NH:8][C:6]1[CH:5]=[C:4]([Cl:14])[N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:12])[CH3:13])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86728315HCID 86728315, compound

Product 1

HCID 86728316HCID 86728316, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-((2,6-dichloropyrimidin-4-yl)amino)-2-methylpropan-1-ol (6.67 g, 28.3 mmol) and triethylamine (11.59 mL, 85 mmol) in dichloromethane (DCM) (100 mL) was added dropwise MsCl (4.40 mL, 56.5 mmol) at 0° C. The reaction mixture was stirred at rt for 2 h, diluted with DCM (100 mL), washed with water (50 mL×3) then brine (50 mL×2), dried over Na2SO4, filtered and concentrated to give the residue as a yellow solid, which was used for the next step without further purification.

Workup

  1. washwashed with water (50 mL×3)
  2. dry with materialbrine (50 mL×2), dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-62f4fc489360464f8ea8426c823336c2
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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