1-Methylpyrrolidine → HCID 67194093, compound

HRID 2401314Notes

Reaction equation

HRID 2401314 reaction equation
Cl[C:2]1[N:3]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:4](=[O:24])[C:5]2[N:6]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:7]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:8][C:9]=2[N:10]=1.CN1CCCC1.C(=O)([O-])[O-].[K+].[K+].[CH3:41][C:42]1[C:47]([OH:48])=[CH:46][CH:45]=[CH:44][N:43]=1>O>[CH:11]1([C:7]2[N:6]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:5]3[C:4](=[O:24])[N:3]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:2]([O:48][C:47]4[C:42]([CH3:41])=[N:43][CH:44]=[CH:45][CH:46]=4)=[N:10][C:9]=3[N:8]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 84541-MethylpyrrolidineHCID 11430Potassium CarbonateHCID 707192-Methylpyridin-3-olHCID 67194473HCID 67194473, compound

Product 1

HCID 67194093HCID 67194093, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
87.5 °C

Procedure

A mixture of 2-chloro-8-cyclopentyl-1-isobutyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.11 g, 0.259 mmol), N-methylpyrrolidine (1 ml), potassium carbonate (0.11 g, 0.778 mmol) and 2-methyl 3-hydroxy pyridine (0.034 g, 0.31 mmol), was heated at 85-90° C. overnight. Reaction mixture was cooled room temperature, diluted with water (10 ml), extracted with ethyl acetate. The ethyl acetate layer was washed with brine and water, dried over sodium sulphate, filtered and concentrated to obtain 8-cyclopentyl-1-isobutyl-2-(2-methyl-pyridin-3-yloxy)-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.11 g, 75%) as crude oil.

Workup

  1. customReaction mixture
  2. temperaturewas cooled room temperature
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with brine and water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-859096dddb224933b4d672d9c57a2460
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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