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Water → HCID 19608363, compound

HRID 1602879
Notes
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Reaction equation

HRID 1602879 reaction equation
[CH2:1]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:8]2[N:19]=[CH:20][CH:21]=[C:7]2[N:6]=1)[CH2:2][CH:3]=[CH2:4].C1C(=O)N([Br:29])C(=O)C1.O>C(COC)OC.O>[Br:29][C:21]1[CH:20]=[N:19][N:8]2[C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:10][C:5]([CH2:1][CH2:2][CH:3]=[CH2:4])=[N:6][C:7]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 9925691HCID 9925691, compound2×

Product 1

HCID 19608363HCID 19608363, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-(3-Butenyl)-7-(4-pyridylmethoxy)pyrazolo[1,5-a]pyrimidine (compound of Example 1), 500 mg, was dissolved in 10 ml of dimethoxyethane-water (3:1). The solution was cooled to 0° C. and 380 mg of NBS was added. The mixture was stirred at 0° C. for 1 hour and further stirred at room temperature for 1 hour. Water was added to the reaction mixture and the crystals precipitated were collected by filtration. The crude crystals were recrystallized from dichloromethane-n-hexane to provide 440 mg of the title compound as colorless crystals. The structure and melting point of the compound obtained are shown in Table 1.

Workup

  1. stirringfurther stirred at room temperature for 1 hour
  2. customthe crystals precipitated
  3. filtrationwere collected by filtration
  4. customThe crude crystals were recrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-29521f189ae341d2855afa7aeb173097
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05985882

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes