Potassium Carbonate → {4-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]phenyl}methanol

HRID 1925940Notes

Reaction equation

HRID 1925940 reaction equation
[Cl:1][C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].[OH:17][CH2:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C)C=O.O>[Cl:1][C:2]1[C:3]2[N:10]([CH2:23][C:22]3[CH:25]=[CH:26][C:19]([CH2:18][OH:17])=[CH:20][CH:21]=3)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5107660[4-(Chloromethyl)phenyl]methanolHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 86084732{4-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]phenyl}methanolYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (307 mg) was dissolved in N,N-dimethylformamide (2 mL), potassium carbonate (304 mg) was added, and the mixture was stirred at room temperature for 30 min. 4-Hydroxymethylbenzyl chloride (377 mg) was added, and the mixture was stirred at room temperature for 16 hrs. After diluting with water (30 mL), the mixture was extracted with ethyl acetate/tetrahydrofuran (3:1, 80 mL×2). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→0:100) to give the title compound (383 mg) as a powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hrs
  2. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran (3:1, 80 mL×2)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→0:100)

Sources & evidence

ORD record
ord-a175abc612d54552a2c4703d3dc5764c
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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