Water → 6-Ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carboxamide

HRID 256317Notes

Reaction equation

HRID 256317 reaction equation
[CH2:1]([C:3]1[C:4]([O:15][CH3:16])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([C:13]#[N:14])[N:12]=2)[C:8]=1[CH3:9])[CH3:2].C(Cl)(Cl)Cl.[OH2:21]>>[CH2:1]([C:3]1[C:4]([O:15][CH3:16])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([C:13]([NH2:14])=[O:21])[N:12]=2)[C:8]=1[CH3:9])[CH3:2]

Participants

4

Reactant 3

HCID 962WaterHCID 6212ChloroformHCID 13669915HCID 13669915, compound

Product 1

HCID 136699166-Ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carboxamideYield 97%

Procedure

A suspension of 10.0 g of 6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carbonitrile of Step A and 20.0 g of Amberlite IRA-400 (base form) in 200 ml of water was stirred rapidly at reflux and after 41/2 hours, the mixture was cooled. Chloroform was added to dissolve the precipitated product and the two phase mixture was filtered to remove the Amberlite. The layers were separated and the aqueous phase was extracted with chloroform. The combined chloroform layers were dried over MgSO4, filtered and evaporated to dryness. The solid product was crystallized from methanol to obtain 10.5 g (97% yield) of 6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carboxamide as white needles melting at 256°-259° C.

Workup

  1. temperatureat reflux
  2. temperatureafter 41/2 hours, the mixture was cooled
  3. dissolutionto dissolve the precipitated product
  4. filtrationthe two phase mixture was filtered
  5. customto remove the Amberlite
  6. customThe layers were separated
  7. extractionthe aqueous phase was extracted with chloroform
  8. dry with materialThe combined chloroform layers were dried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe solid product was crystallized from methanol

Sources & evidence

ORD record
ord-165bee62dee44255818eaae990430ae1
Source dataset
uspto-grants-1987_10
Patent number
US04703049

Reaction notes

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