Water → 2-(4-Fluorophenyl)pyrazolo[1,5-a]pyrimidine

HRID 570139Notes

Reaction equation

HRID 570139 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([NH2:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.CO[CH:16](OC)[CH2:17][CH:18](OC)OC.O.[NH4+].[OH-]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]3[N:13]=[CH:16][CH:17]=[CH:18][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 66019TetramethoxypropaneHCID 178507289HCID 178507289, compound

Product 1

HCID 692972612-(4-Fluorophenyl)pyrazolo[1,5-a]pyrimidineYield 113.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-(4-fluorophenyl)-1H-pyrazole-5-amine (5.0 g, 0.028 mol) in acetic acid (50 mL) is added 1,1,3,3-tetramethoxypropane (5.79 g, 0.035 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. 6.8 g (79%) of 2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine are obtained as a beige solid which is used in the next step without further purification.

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

Sources & evidence

ORD record
ord-3038946df37a46779917edd8faa827d2
Source dataset
uspto-grants-2015_05
Patent number
US09023844B2

Reaction notes

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