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Triethylamine → 2-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethyl methanesulfonate

HRID 928567
Notes
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Reaction equation

HRID 928567 reaction equation
[CH:1]([C:4]1[C:12]2[C:11]([N:13]3[CH2:18][CH:17]4[CH2:19][CH:14]3[CH2:15][CH:16]4[O:20][CH2:21][CH2:22][OH:23])=[N:10][CH:9]=[N:8][C:7]=2[S:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([O:23][CH2:22][CH2:21][O:20][CH:16]1[CH2:15][CH:14]2[CH2:19][CH:17]1[CH2:18][N:13]2[C:11]1[C:12]2[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][S:6][C:7]=2[N:8]=[CH:9][N:10]=1)(=[O:34])=[O:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 895794632-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethanol

Product 1

HCID 895794842-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethyl methanesulfonateYield 106.8%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

2-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethanol (0.56 g, 1.7 mmol) was stirred in DCM (13.25 g, 10 mL, 156.0 mmol) at 0° C. Triethylamine (0.52 g, 0.71 mL, 5.0 mmol) was added. Methanesulfonyl chloride (0.29 g, 0.20 mL, 2.5 mmol) was added dropwise and the reaction allowed to warm slowly to room temperature and stirred for 1 hour. The reaction mixture was diluted with DCM, washed with water, dried over Na2SO4 and concentrated in vacuo to afford 2-[[2-(5-isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethyl methanesulfonate (0.747 g). LCMS RT=3.94 min. M+1=412.

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa0dcbdc268d4261aa94a7aea55c5f6f
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290511B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes