Acetic Acid → 8-Chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

HRID 479290Notes

Reaction equation

HRID 479290 reaction equation
Br.[NH2:2][C:3]1[N:7]2[C:8](SC)=[N:9][CH:10]=[C:11]([Cl:12])[C:6]2=[N:5][N:4]=1.[C:15](OCC)(=[O:18])C=C.C[O-].[Na+].C(O)(=O)C>CO>[NH2:2][C:3]1[N:7]=[C:6]2[N:5]([C:8]([O:18][CH3:15])=[N:9][CH:10]=[C:11]2[Cl:12])[N:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 10942334Sodium MethoxideHCID 18769968HCID 18769968, compound

Product 1

HCID 187699738-Chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 15.0 g (51 mmol) of 3-amino-8-chloro-5-methylthio[1,2,4]triazolo[4,3-c]pyrimidine hydrobromide, 8.2 mL (76 mmol) of ethyl acrylate, and 150 mL of methanol was prepared and cooled in an ice bath. A solution of 17 mL (76 mmol) of 4.5 molar sodium methoxide in methanol was added to this slowly with cooling and stirring. When the addition was complete, the mixture was allowed to warm to ambient temperature and was stirred for 18 hours. It was then neutralized with 2.0 mL of acetic acid. The solids that formed were recovered by filtration, washed with diethyl ether, and dried to obtain 7.7 g (75 percent of theory) of the title compound as a tan powder melting above 250° C. 1H NMR (DMSO-d6): δ 8.0(s, 1H); 6.6 (brs, 2H); 4.1 (s, 3H); 13C: δ 166.40, 151.65, 147.73, 140.95, 108.57, 56.12. Anal. Calc'd for C6H6N5ClO: C, 36.1; H, 3.03; N, 35.1. Found: C, 36.1; H, 3.19; N, 34.8.

Workup

  1. customwas prepared
  2. temperaturecooled in an ice bath
  3. temperaturewith cooling
  4. additionWhen the addition
  5. stirringwas stirred for 18 hours
  6. customThe solids that formed
  7. filtrationwere recovered by filtration
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-6c0bd389b73f4c0b98efd159671c14ba
Source dataset
uspto-grants-2003_11
Patent number
US06645918B1

Reaction notes

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