Sodium hydride → HCID 90034967, compound

HRID 1481312

Reaction equation

HRID 1481312 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[NH2:7].[H-].[Na+].[CH3:10][Si:11]([CH2:14][CH2:15][O:16][CH2:17]Cl)([CH3:13])[CH3:12]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:17][O:16][CH2:15][CH2:14][Si:11]([CH3:13])([CH3:12])[CH3:10])[C:6]=1[NH2:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1400793-Amino-4-bromopyrazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 90034967HCID 90034967, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-1H-pyrazol-5-amine (1 g, 6.17 mmol) in THF (20 mL) at 0° C. was added NaH (0.494 g, 12.35 mmol) and stirred at the same temperature for 30 mins To this mixture was then added SEM-Cl (1.095 mL, 6.17 mmol) and slowly allowed to raise to rt and stirred at rt for 1 h. The reaction mix was then quenched with Satd. NH4Cl and then extracted with EtOAc, dried over Na2SO4, filtered, and concentrated. Purification by normal phase chromatography afforded 221A (1.45 g, 80% yield) as a pale yellow oil. MS (ESI) m/z: 292.0 (M+H)+.

Workup

  1. stirringstirred at rt for 1 h
  2. additionThe reaction mix
  3. customwas then quenched with Satd
  4. extractionNH4Cl and then extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-5339d04b8649486f81a9b6b40a30b900
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Linked notes

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