Dimethylformamide → 5-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)pentyl acetate

HRID 1926066Notes

Reaction equation

HRID 1926066 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:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br)(=[O:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=[CH:9]1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 851405-Bromopentyl acetateHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 568508045-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)pentyl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (0.50 g), 5-bromopentyl acetate (0.71 mL), cesium carbonate (1.59 g) and N,N-dimethylformamide (5.0 mL) was stirred at 40° C. for 4 days. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate:hexane=1:3→6:4) to give the title compound (637 mg) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was separated
  6. custompurified by silica gel column chromatography (eluent, ethyl acetate:hexane=1:3→6:4)

Sources & evidence

ORD record
ord-616d52d63e2d463d918058935b8bec2b
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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