1-Acetoxy-2-bromoethane → HCID 67494487, compound

HRID 2047074Notes

Reaction equation

HRID 2047074 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[CH:14]=[N:15][N:16]4[C:21]([N:22]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:20][C:19]([C:39]5[CH:40]=[N:41][NH:42][CH:43]=5)=[N:18][C:17]=34)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:46]([O:49][CH2:50][CH2:51]Br)(=[O:48])[CH3:47]>CN(C=O)C>[C:46]([O:49][CH2:50][CH2:51][N:41]1[CH:40]=[C:39]([C:19]2[CH:20]=[C:21]([N:22]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:37])[CH3:38])[N:16]3[N:15]=[CH:14][C:13]([C:10]4[CH:11]=[N:12][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][CH:9]=4)=[C:17]3[N:18]=2)[CH:43]=[N:42]1)(=[O:48])[CH3:47]

Participants

5

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 136391021HCID 136391021, compound

Product 1

HCID 67494487HCID 67494487, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 2-5 mL pressure vial was charged 3-(6-phenylpyridin-3-yl)-5-(1H-pyrazol-4-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.38 mmol, 230 mg), DMF (4 mL), and sodium hydride (40% w/w in mineral oil, 0.56 mmol, 23 mg). This suspension was sonicaided and allowed to stir at room temperature for 15 minutes. At 15 minutes, 2-bromoethyl acetate (0.56 mmol, 62 μL). The vial was then sealed and the reaction was stirred at 80° C. for 18 hours. After 18 hours, the solvent was removed in vacuo, and the resulting residue was purified by flash chromatography to yield the title compound.

Workup

  1. waitAt 15 minutes
  2. customThe vial was then sealed
  3. stirringthe reaction was stirred at 80° C. for 18 hours
  4. waitAfter 18 hours
  5. customthe solvent was removed in vacuo
  6. customthe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-92af7426bc0d47e695bcf1b6fbf918e3
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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