2-Aminopyrimidine → HCID 20145062, compound

HRID 1906000Notes

Reaction equation

HRID 1906000 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12](=O)[CH2:13]Br)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[NH2:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(N(CC)CC)C>C(O)C>[NH2:1][C:2]1[S:3][C:4]([C:12]2[N:16]=[C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]3[CH:13]=2)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 79782-AminopyrimidineHCID 8471TriethylamineHCID 20145096Ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate

Product 1

HCID 20145062HCID 20145062, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate (5.9 g), 2-aminopyrimidine (5.7 g) and triethylamine (8.4 ml) in ethanol (100 ml) was refluxed for 6 hours. The reaction mixture was evaporated in vacuo. To the residue was added a mixture of water and ethyl acetate, and the resulting mixture was acidified to pH 0.5 with conc. hydrochloric acid. The separated aqueous layer was treated with charcoal and filtered. To the filtrate was added ethyl acetate and the resulting mixture was adjusted to pH 7.0 and 20% aqueous potassium carbonate. The precipitate was collected by filtration, washed successively with water, ethyl acetate and ethanol, and dried over phosphorus pentoxide to give 2-(2-amino-4-ethoxycarbonyl-5-thiazolyl)imidazo[1,2-a]pyrimidine (1.6 g). mp 282° C. (dec.)

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionTo the residue was added
  3. additiona mixture of water and ethyl acetate
  4. additionThe separated aqueous layer was treated with charcoal
  5. filtrationfiltered
  6. additionTo the filtrate was added ethyl acetate
  7. filtrationThe precipitate was collected by filtration
  8. washwashed successively with water, ethyl acetate and ethanol
  9. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-e47be2c80a064755b869db8a68c11263
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

Loading…