Water → HCID 57191409, compound

HRID 2248361Notes

Reaction equation

HRID 2248361 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]=[N:9][N:8]([CH:11]3[CH2:15][CH2:14][CH:13]=[CH:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH2:16].C[N+]1([O-])CCOCC1.[OH2:25]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[NH2:1][C:2]1[C:3]2[N:10]=[N:9][N:8]([C@@H:11]3[CH2:15][CH2:14][C@@H:13]([OH:16])[C@H:12]3[OH:25])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 19996042HCID 19996042, compound

Product 1

HCID 57191409HCID 57191409, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent2×

Conditions

Temperature
25 °C

Procedure

(±)-7-Amino-3-(2-cyclopenten-1-yl)-1,2,3-triazolo[4,5-d]pyrimidine (4.80 g, 23.7 mmol), N-methylmorpholine N-oxide monohydrate (3.15 g, 26.1 mmol as 97%), water (35 ml), t-butylalcohol (175 ml) and 2.5% osmium tetroxide in t-butyl alcohol (1.0 ml) were refluxed for 3 hours and then stirred at 25° C. for 18 hours. The resulting mixture was evaporated to dryness and chromatographed on silica gel. Title compound was eluted with MeOH:CHCl3 /1:3 to give white crystals after two recrystallizations from ethanol-water (3.74 g, 67%); mp 244°-245° C.; 1H-NMR (Me2SO-d6) δ8.26 (s, 1, H-5'), 8.35 and 8.05 (both br s) overlapping 8.26 (s) (total 3 protons, tautomers NH2 and H-5'), 5.2-5.0 (m) overlapping 5.01 (d, J=7.3) (total 2, OH and H-3 ), 4.72 (d, J=3.5, 1, OH), 4.5-4.4 (m, 1, H-2), 4.1-4.0 (m, 1, H-1), 2.4-1.6 (m, 4, two CH2).

Workup

  1. customThe resulting mixture was evaporated to dryness
  2. customchromatographed on silica gel
  3. washTitle compound was eluted with MeOH
  4. customCHCl3 /1:3 to give white crystals
  5. customafter two recrystallizations from ethanol-water (3.74 g, 67%)

Sources & evidence

ORD record
ord-73e1d5a368e84a9ea64e4c30d2673d78
Source dataset
uspto-grants-1991_08
Patent number
US05039689

Reaction notes

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