Ammonia → HCID 18382530, compound

HRID 2297602Notes

Reaction equation

HRID 2297602 reaction equation
[CH2:1]([N:8]1[C:12]2[C:13](=[O:24])[N:14]([CH2:22][CH3:23])[C:15]3[N:16]([N:17]=[C:18]([CH:20]=O)[N:19]=3)[C:11]=2[N:10]=[C:9]1[CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:30]>CO.[Pd]>[NH2:30][CH2:20][C:18]1[N:19]=[C:15]2[N:14]([CH2:22][CH3:23])[C:13](=[O:24])[C:12]3[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:9]([CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[N:10][C:11]=3[N:16]2[N:17]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 18382510HCID 18382510, compound

Product 1

HCID 18382530HCID 18382530, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2 g of 6-benzyl-7-cyclopentyl-4-ethyl-2-formyl-imidazo[4.5-e]-s-triazolo[1.5-a]pyrimidin-5-one (for preparation see synthesis example II) are hydrogenated together with 1 g of ammonia in 30 ml of methanol on 0.2 g of 10% palladium on charcoal (5 bar, 20° C., 2.3 hours). For working up, the catalyst is filtered off and the solvent is distilled off in vacuo. The crude product is purified by chromatography on silica gel (dichloromethane:methanol 95:5) and yields 0.65 g of the title compound in the form of a colourless amorphous solid.

Workup

  1. filtrationthe catalyst is filtered off
  2. distillationthe solvent is distilled off in vacuo
  3. customThe crude product is purified by chromatography on silica gel (dichloromethane:methanol 95:5)

Sources & evidence

ORD record
ord-be1f7621332a434a907a8afa2d430884
Source dataset
uspto-grants-2002_12
Patent number
US06492377B1

Reaction notes

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