Bromine → HCID 86697422, compound

HRID 1478249Notes

Reaction equation

HRID 1478249 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][O:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][N:14]2[N:17]=[CH:18][CH:19]=[C:13]2[N:12]=1.[Br:20]Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[Br:20][C:19]1[CH:18]=[N:17][N:14]2[CH:15]=[CH:16][C:11]([NH:10][CH2:9][CH2:8][O:7][CH3:6])=[N:12][C:13]=12

Participants

7

Reactant 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 86697420HCID 86697420, compound

Product 1

HCID 86697422HCID 86697422, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

Sodium acetate [127-09-3] (457.6 mg, 5.6 mmol) was added to a solution of N-(2-methoxyethyl)pyrazolo[1,5-a]pyrimidin-5-amine (706.4 mg, 3.7 mmol) in glacial acetic acid (40 mL) and allowed to stir at ambient temperature until all of the solid had dissolved. Bromine [7726-95-6] (0.2 mL, 3.7 mmol) was added into the ambient temperature, buffered acetic acid reaction solution over 2 minutes, then the reaction solution was slowly poured into stirring water (1 L). The pH was increased by the addition of solid sodium bicarbonate until the pH of the supernatant was determined to be approximately 8 by pH paper. Precipitated product was isolated by filtration, the filter cake washed with water, and allowed to dry to afford 819.6 mg of white powder. LRMS (ESI) m/z 271.0/273.0 [(M+H)]+, calc'd for C9H11BrN4O: 271.12.

Workup

  1. dissolutionhad dissolved
  2. additionthe reaction solution was slowly poured
  3. customPrecipitated product was isolated by filtration
  4. washthe filter cake washed with water
  5. customto dry

Sources & evidence

ORD record
ord-0cd505d735ab48f39b2a804f937fe03a
Source dataset
uspto-grants-2016_08
Patent number
US09403832B2

Reaction notes

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