Water → HCID 57691107, compound

HRID 219116Notes

Reaction equation

HRID 219116 reaction equation
[N:1]([CH2:4][C:5]1[N:9]2[N:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=[N:13][C:8]2=[N:7][N:6]=1)=[N+]=[N-].C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>>[C:14]1([C:11]2[CH:12]=[N:13][C:8]3[N:9]([C:5]([CH2:4][NH2:1])=[N:6][N:7]=3)[N:10]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 57691362HCID 57691362, compound

Product 1

HCID 57691107HCID 57691107, compound

Procedure

A 50 mL RB flask was charged with 3-(azidomethyl)-6-phenyl-[1,2,4]triazolo[4,3-b][1,2,4]triazine (0.3492 g, 1.38 mmol) and THF (14.0 ml, 171 mmol), resulting in a dark brown solution. Triphenylphosphine (0.545 g, 2.08 mmol) and water (0.0998 ml, 5.54 mmol) were added, and the flask was placed in a 65° C. oil bath for 2 hours. The reaction mixture was concentrated to give a thick brown oil, which was purified by column chromatography using an 80 g ISCO column, eluting with a gradient of 5% MeOH (containing NH4OH)/DCM to 10% MeOH (containing NH4OH)/DCM over 40 minutes. (6-phenyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl)methanamine was isolated as a yellow solid.

Workup

  1. customresulting in a dark brown solution
  2. customwas placed in a 65° C.
  3. customfor 2 hours
  4. concentrationThe reaction mixture was concentrated
  5. customto give a thick brown oil, which
  6. customwas purified by column chromatography
  7. washeluting with a gradient of 5% MeOH (containing NH4OH)/DCM to 10% MeOH (containing NH4OH)/DCM over 40 minutes

Sources & evidence

ORD record
ord-57f8e2d711464959af8ef236ce7ea8e9
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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