m-Chloroperbenzoic acid → N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047168Notes

Reaction equation

HRID 2047168 reaction equation
S1CCC([C:7]2[CH:12]=[C:11]([N:13]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:10]3[N:30]=[CH:31][CH:32]=[C:9]3[N:8]=2)CC1.C1C=C(Cl)C=C(C(OO)=O)C=1>>[CH3:27][Si:26]([CH3:29])([CH3:28])[CH2:25][CH2:24][O:23][CH2:22][N:13]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:11]1[N:10]2[N:30]=[CH:31][CH:32]=[C:9]2[N:8]=[CH:7][CH:12]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 665844755-(tetrahydro-2H-thiopyran-4-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 68757881N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

Procedure

To a solution of compound, 5-(tetrahydro-2H-thiopyran-4-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (18.7 mmol, 9.23 g) DCM (100 mL) was added mCPBA and stirred at rt for 1 h. The reaction was quenched with Na2S2O3 (aq.) and diluted with DCM (100 mL). The separated organic layer was washed with NaHCO3 (2*) and brine, dried over Na2SO4, and concentrated to afford crude compound, 5-(tetrahydro-2H-thiopyran-4-yl-1′,1′-dioxide)-)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine as a purple oil, which was used without further purification. HPLC-MS TR=2.72 min (UV 254 nm, 5 min method); mass calculated for formula C23H42N4O4SSi2 526.2, observed LCMS m/z 527.2 (M+H).

Workup

  1. customThe reaction was quenched with Na2S2O3 (aq.)
  2. additiondiluted with DCM (100 mL)
  3. washThe separated organic layer was washed with NaHCO3 (2*) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eddbd05de6814d9891c0368da070c796
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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