Acetic Acid → HCID 136009386, compound

HRID 1969578Notes

Reaction equation

HRID 1969578 reaction equation
[CH:1]1[N:5]2[C:6]3[CH:12]=[CH:11][NH:10][C:7]=3[N:8]=[CH:9][C:4]2=[N:3][N:2]=1.C1N2CN3CN(C2)CN1C3.[C:23](O)(=[O:25])C>O>[CH:1]1[N:5]2[C:6]3[C:12]([CH:23]=[O:25])=[CH:11][NH:10][C:7]=3[N:8]=[CH:9][C:4]2=[N:3][N:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 136009486HCID 136009486, compound

Product 1

HCID 136009386HCID 136009386, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

Water (1.0 mL) was added to a mixture of 6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.200 g, 1.26 mmol, prepared using D from Preparation #BBBBB.1 and NaOH) and hexamethylenetetramine (0.264 g, 1.89 mmol). Acetic acid (0.5 mL) was added. The reaction vessel was sealed and the mixture was warmed to about 100° C. After about 8 h, the solution was allowed to cool to ambient temperature. After sitting for about 13 h, the mixture was cooled to about 0° C. The resulting mixture was diluted with water (1 mL) and then filtered rinsing with water. The solid was dried to afford 6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine-8-carbaldehyde (0.041 g, 18%): LC/MS (Table 1, Method n) Rt=0.23 min; MS m/z 188 (M+H)+.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureto cool to ambient temperature
  3. waitAfter sitting for about 13 h
  4. temperaturethe mixture was cooled to about 0° C
  5. filtrationfiltered
  6. washrinsing with water
  7. customThe solid was dried

Sources & evidence

ORD record
ord-df59c4107bb94fb8950c6e75d2c622e4
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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