m-Chloroperbenzoic acid → HCID 86686669, compound

HRID 334374Notes

Reaction equation

HRID 334374 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[C:12]([N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:11]3[N:31]=[CH:32][C:33]([C:34]4[CH:35]=[N:36][C:37]([C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)=[CH:38][CH:39]=4)=[C:10]3[N:9]=2)[CH2:4][CH2:3]1.C1C=C(Cl)C=C(C(OO)=[O:54])C=1>C(Cl)Cl>[C:40]1([C:37]2[N:36]=[CH:35][C:34]([C:33]3[CH:32]=[N:31][N:11]4[C:12]([N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])=[CH:13][C:8]([CH:5]5[CH2:4][CH2:3][C:2]6([O:54][CH2:1]6)[CH2:7][CH2:6]5)=[N:9][C:10]=34)=[CH:39][CH:38]=2)[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86686670HCID 86686670, compound

Product 1

HCID 86686669HCID 86686669, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(4-methylenecyclohexyl)-3-(6-phenylpyridin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (455 mg, 0.709 mmol) in DCM (4 mL) at 0° C. was added a solution of m-CPBA (191 mg, 0.850 mmol) in DCM (3 mL). The resulting mixture was warmed to rt and stirred for 4 h. All the volatiles were removed under reduced pressure and the residue was purified by a SiO2 column (0-20% EtOAc/Hexanes, Rf=0.25 in 20% EtOAc) to afford 3-(6-phenylpyridin-3-yl)-5-(1-oxaspiro[2.5]octan-6-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine as a pale yellow oil (163 mg). HPLC-MS TR=3.32 min (UV 254 nm, 5 min method); mass calculated for formula C36H51N5O3Si2 657.4, observed LCMS m/z 658.3 (M+H).

Workup

  1. customAll the volatiles were removed under reduced pressure
  2. customthe residue was purified by a SiO2 column (0-20% EtOAc/Hexanes, Rf=0.25 in 20% EtOAc)

Sources & evidence

ORD record
ord-ab244088a52b489997afa93024f33eb0
Source dataset
uspto-grants-2014_11
Patent number
US08883801B2

Reaction notes

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