Methylparaben → Methyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yloxy)benzoate

HRID 2047048Notes

Reaction equation

HRID 2047048 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:18]2[N:38]=[CH:39][CH:40]=[C:17]2[N:16]=1.[NH4+].[Cl-]>CN(C=O)C>[CH3:35][Si:34]([CH3:37])([CH3:36])[CH2:33][CH2:32][O:31][CH2:30][N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:19]1[N:18]2[N:38]=[CH:39][CH:40]=[C:17]2[N:16]=[C:15]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 772312195-chloro-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 66737940Methyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yloxy)benzoateYield 899.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The methyl 4-hydroxybenzoate (330 mg, 0.2 mmol) was dissolved in dry DMF (3 mL) and NaH (8 mg, 60% in oil, 0.2 mmol) was added and the mixture was stirred at room temperature for 5 min. Then, 5-chloro-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (430 mg, 0.1 mmol) was added and the resulting mixture was heated up to 130° C. with Microwave and stirred for 30 min. After cooling to room temperature, NH4Cl (aq) was added to quench the reaction and extracted with EtOAc (50 mL×3). The combined organics were washed with water and brine and dried over Na2SO4. After concentration, the residue was purified with column (silica gel, 20% EtOAc/Hexane) gave the product, methyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yloxy)benzoate (490 mg) as clear oil. HPLC-MS tR=2.84 min (UV254 nm); mass calculated for formula C26H40N4O5Si2 544.3, observed LCMS m/z 545.3 (M+H).

Workup

  1. temperaturethe resulting mixture was heated up to 130° C. with Microwave
  2. stirringstirred for 30 min
  3. temperatureAfter cooling to room temperature
  4. customto quench
  5. customthe reaction
  6. extractionextracted with EtOAc (50 mL×3)
  7. washThe combined organics were washed with water and brine
  8. dry with materialdried over Na2SO4
  9. concentrationAfter concentration
  10. customthe residue was purified with column (silica gel, 20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-fc729ab7a9db4bcdb6a08ed71ee24c9f
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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