Ammonium Hydroxide → Imidazo[1,2-a]pyrimidine-7-carboxamide

HRID 2183889Notes

Reaction equation

HRID 2183889 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[N:6]=1)=O.[OH-].[NH4+:15]>>[N:13]1[CH:12]=[CH:11][N:8]2[CH:9]=[CH:10][C:5]([C:3]([NH2:15])=[O:2])=[N:6][C:7]=12

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 55264027HCID 55264027, compound

Product 1

HCID 45084616Imidazo[1,2-a]pyrimidine-7-carboxamideYield 58%

Conditions

Temperature
100 °C

Procedure

A mixture of imidazo[1,2-α]pyrimidine-7-carboxylic acid methyl ester (580 mg) and 28% ammonium hydroxide was heated at 100° C. in a sealed tube for 2 h then cooled to ambient temperature. The resulting solid was filtered, washed with ice-cold water and dried under vacuum to give imidazo[1,2-α]pyrimidine-7-carboxylic acid amide (310 mg, 58%) as a white solid: δH (360 MHz, DMSO) 7.61 (1H, d, J 7), 7.77 (1H, s), 7.92 (1H, d, J 1), 8.09 (1H, d, J 1), 8.32 (1H, s), 9.11 (1H, d, J 7).

Workup

  1. temperaturethen cooled to ambient temperature
  2. filtrationThe resulting solid was filtered
  3. washwashed with ice-cold water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ce5797e2882743e9afb809d0394b4c59
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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