Water → HCID 83744419, compound

HRID 570138Notes

Reaction equation

HRID 570138 reaction equation
[Br:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][NH:5][C:6]=1[NH2:7].CO[CH:16](OC)[CH2:17][CH:18](OC)OC.O.[NH4+].[OH-]>C(O)(=O)C>[Br:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][N:5]2[CH:18]=[CH:17][CH:16]=[N:7][C:6]=12

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 66019TetramethoxypropaneHCID 5943194-Bromo-3-phenyl-1H-pyrazol-5-amine

Product 1

HCID 83744419HCID 83744419, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-bromo-3-phenyl-1H-pyrazole-5-amine (5.0 g, 0.02 mol) in acetic acid (50 mL) is added 1,1,3,3-tetramethoxypropane (4.14 g, 0.025 mol). The mixture is stirred at 110° C. for 1 h. The reaction mixture is then poured into water, basified with NH4OH and extracted with dichloromethane (3×100 mL). The organic layer is dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material is purified by column chromatography using silica gel in dichloromethane and ethyl acetate (1:0 to 95:5) as eluent and 4.2 g (75%) of 3-bromo-2-phenylpyrazolo[1,5-a]pyrimidine are obtained as a beige solid.

Workup

  1. extractionextracted with dichloromethane (3×100 mL)
  2. dry with materialThe organic layer is dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-32df2614b91f4eb19b253315662d9639
Source dataset
uspto-grants-2015_05
Patent number
US09023844B2

Reaction notes

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