Phenol → HCID 56850808, compound

HRID 1926093Notes

Reaction equation

HRID 1926093 reaction equation
Cl[C:2]1[C:3]2[N:10]([CH2:11][CH:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>C(OCC)(=O)C>[O:25]([C:2]1[C:3]2[N:10]([CH2:11][CH:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 56850807HCID 56850807, compound

Product 1

HCID 56850808HCID 56850808, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-chloro-5-(2,2-diethoxyethyl)-5H-pyrrolo[3,2-d]pyrimidine (1 g), phenol (420 mg), potassium carbonate (617 mg) and 1-methyl-2-pyrrolidone (6.74 mL) was stirred with heating at 140° C. for 6 hrs. The reaction mixture was diluted with ethyl acetate (100 mL), and washed with water (80 mL). The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→40/60) to give the title compound (1.15 g) as a yellow oil.

Workup

  1. washwashed with water (80 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→40/60)

Sources & evidence

ORD record
ord-c494fed1890d469483f5425155dd7d90
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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