2-Aminopyrimidine → HCID 20144976, compound

HRID 1905996Notes

Reaction equation

HRID 1905996 reaction equation
Br.[NH2:2][C:3]1[S:4][C:5]([C:9](=O)[CH2:10]Br)=[C:6]([CH3:8])[N:7]=1.[NH2:13][C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(N(CC)CC)C>C(O)C>[NH2:2][C:3]1[S:4][C:5]([C:9]2[N:13]=[C:14]3[N:19]=[CH:18][CH:17]=[CH:16][N:15]3[CH:10]=2)=[C:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 79782-AminopyrimidineHCID 8471TriethylamineHCID 20145033HCID 20145033, compound

Product 1

HCID 20144976HCID 20144976, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-amino-4-methyl-5-(2-bromoacetyl)thiazole hydrobromide (7.2 g), 2-aminopyrimidine (3.8 g) and triethylamine (11 ml) in ethanol (200 ml) was refluxed for 8 hours and the reaction mixture was evaporated in vacuo. To the residue was added water and the resulting mixture was acidified to pH 1.0 with 10% hydrochloric acid. The acidified solution was treated with charcoal and filtered. The filtrate was adjusted to pH 7.0 with 20% aqueous potassium carbonate. The resulting precipitate was collected by filtration, washed successively with water and ethyl acetate, and recrystallized from aqueous ethanol to give 2-(2-amino-4-methyl-5-thiazolyl)imidazo[1,2-a]pyrimidine (0.8 g). mp 285°-286° C. (dec.)

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. additionTo the residue was added water
  3. additionThe acidified solution was treated with charcoal
  4. filtrationfiltered
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed successively with water and ethyl acetate
  7. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-f106d26f6cb248578f6e576cd50d0b06
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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