Sodium Hydroxide → HCID 20324952, compound

HRID 838855Notes

Reaction equation

HRID 838855 reaction equation
[CH2:1]([C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH3:14])[N:8]2[N:15]=[CH:16][CH:17]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].[Br:18]N1C(=O)CCC1=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:18][C:17]1[CH:16]=[N:15][N:8]2[C:9]([CH2:11][CH2:12][CH2:13][CH3:14])=[CH:10][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][C:7]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 203249445,7-Dibutylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 20324952HCID 20324952, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 7.0 g (0.03 mol) of 5,7-di-n-butylpyrazolo[1,5-a]-pyrimidine in 75 ml chloroform was treated with 5.8 g (0.035 mol) of N-bromosuccinimide at room temperature. The mixture was stirred for 5-10 minutes, then poured into ice water, made alkaline with 6N NaOH, and the organic layer separated and dried (Na2SO4). The chloroform solution was chromatographed on neutral alumina (Woelm, grade I) with chloroform as the eluant. Evaporation of the solvent and recrystallization from ligroine gave 7.15 g (72%) of the product, mp 47°-48° C.

Workup

  1. customthe organic layer separated
  2. dry with materialdried (Na2SO4)
  3. customThe chloroform solution was chromatographed on neutral alumina (Woelm, grade I) with chloroform as the eluant
  4. customEvaporation of the solvent and recrystallization from ligroine

Sources & evidence

ORD record
ord-97b69ec5311349f7bc3f44710ecb64a4
Source dataset
uspto-grants-1978_06
Patent number
US04093617

Reaction notes

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