Potassium Carbonate → HCID 57988784, compound

HRID 889014Notes

Reaction equation

HRID 889014 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([C:22]3[CH:23]=[N:24][NH:25][CH:26]=3)=[N:8][C:7]=2[N:6]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:5]1=[O:35])[CH2:2][CH3:3].Br[CH2:37][C:38]#[C:39][C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([C:22]3[CH:23]=[N:24][N:25]([CH2:37][C:38]#[C:39][C:40]4[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=4)[CH:26]=3)=[N:8][C:7]=2[N:6]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[C:5]1=[O:35])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15049976HCID 15049976, compoundHCID 57988761HCID 57988761, compound

Product 1

HCID 57988784HCID 57988784, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
52.5 °C

Procedure

A mixture of 1-propyl-8-(1H-pyrazol-4-yl)-3,7-bis-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (prepared as per literature procedure US20080194593) (0.1 g, 0.18 mmol), 1-(3-bromo-prop-1-ynyl)-4-methyl-benzene (prepared according to example E1) (0.039 g, 0.18 mmol), potassium carbonate (0.051 g, 0.37 mmol), and acetone (10 ml) were heated at 50-55° C. for 16 hours. Reaction mixture was cooled to 20-25° C. and filtered off. The filtrate was evaporated and residue was purified by preparative TLC to afford 1-propyl-8-[1-(3-p-tolyl-prop-2-ynyl)-1H-pyrazol-4-yl]-3,7-bis-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.035 g, 28%) as a brown sticky mass.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 20-25° C.
  3. filtrationfiltered off
  4. customThe filtrate was evaporated
  5. customresidue was purified by preparative TLC

Sources & evidence

ORD record
ord-d41f774ed639406494cd53d43c1808cd
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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