Triethylamine → HCID 135423037, compound

HRID 989744Notes

Reaction equation

HRID 989744 reaction equation
[OH:1][CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:3]1[NH:4][C:5](=[O:23])[C:6]2[N:11]=[N:10][N:9]([CH:12]([CH3:22])[CH2:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[N:8]=1.C(N(CC)CC)C>CS(C)=O.ClCCl>[C:2]([C:3]1[NH:4][C:5](=[O:23])[C:6]2[N:11]=[N:10][N:9]([CH:12]([CH3:22])[CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:7]=2[N:8]=1)(=[O:1])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 135444679HCID 135444679, compound

Product 1

HCID 135423037HCID 135423037, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

384 mg (0.988 mmol) of 5-(hydroxy-phenyl-methyl)-3-(1-methyl-4-phenyl-butyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one are dissolved in a mixture of 3 ml of DMSO and 10 ml of dichloromethane, and the solution is cooled to 0° C. 1.37 ml (9.88 mmol) of triethylamine and 692 mg (4.35 mmol) of pyridine-SO3 complex are added, and the reaction mixture is then stirred at room temperature for 15 hours. For work-up, the mixture is diluted with 100 ml of dichloromethane and the organic phase is washed with 1N HCl and saturated sodium bicarbonate solution and then dried over sodium sulphate. The solvent is removed, and chromatographic purification gives 185 mg (48%) of a solid, m.p.: 105° C.

Workup

  1. washthe organic phase is washed with 1N HCl and saturated sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. customThe solvent is removed
  4. customchromatographic purification

Sources & evidence

ORD record
ord-1eda5685f32a4224a877b587e88466c3
Source dataset
uspto-grants-2002_10
Patent number
US06458796B1

Reaction notes

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