Carbon Dioxide → HCID 20275275, compound

HRID 370725Notes

Reaction equation

HRID 370725 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]2[NH:8][N:9](C)[CH:10]=[C:4]2[CH:3]=1.[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13].[C:17](=O)=O>O1CCOCC1.C(Cl)(Cl)Cl.CCCCCC>[CH2:12]([N:14]([C:2]1[N:7]=[C:6]([CH3:17])[N:5]2[N:8]=[N:9][CH:10]=[C:4]2[CH:3]=1)[CH2:15][CH3:16])[CH3:13]

Participants

7

Reactant 3

HCID 280Carbon DioxideHCID 8021DiethylamineHCID 20275290HCID 20275290, compound

Product 1

HCID 20275275HCID 20275275, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 2.5 g (15 mmole) of 5-chloro-2-methyltriazolo[1,5-c]pyrimidine in 50 ml of dioxane was added 2.2 g (30 mmole) of N,N-diethylamine. After stirring for three hours at about 20° C., the solid was separated by filtration and washed with dioxane. The filtrate and washings were evaporated to provide a residue which was dissolved in 150 ml of chloroform. The solution was washed thrice with 50 ml portions of water and once with 50 ml of saturated sodium chloride solution, and was then dried over magnesium sulfate. Evaporation of the chloroform provided an oil which solidified when cooled with dry ice. The solid was suspended in hexane, and the mixture was cooled to 0° C. Filtration provided a yellow solid which was purified by high pressure liquid chromatography with chloroform as the eluent. The middle fractions provided a residue which was triturated with diethyl ether and dried. The white solid product was 5-(N,N-diethylamino)-7-methyltriazolo[1,5-c]pyrimidine, m.p. 57°-58° C. Analysis: Calculated for C10H15N5 : %C, 58.5; %H, 7.4; %N, 34.1; Found: %C, 58.4; %H, 7.5; %N, 34.0.

Workup

  1. customthe solid was separated by filtration
  2. washwashed with dioxane
  3. customThe filtrate and washings were evaporated
  4. customto provide a residue which
  5. washThe solution was washed thrice with 50 ml portions of water
  6. dry with materialonce with 50 ml of saturated sodium chloride solution, and was then dried over magnesium sulfate
  7. customEvaporation of the chloroform
  8. customprovided an oil which
  9. temperaturethe mixture was cooled to 0° C
  10. filtrationFiltration
  11. customprovided a yellow solid which
  12. customwas purified by high pressure liquid chromatography with chloroform as the eluent
  13. customThe middle fractions provided a residue which
  14. customwas triturated with diethyl ether
  15. customdried

Sources & evidence

ORD record
ord-3b6ac5c0de7241ad8c59a8c74beecba8
Source dataset
uspto-grants-1985_07
Patent number
US04528288

Reaction notes

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