Water → 9-(3-Bromopropyl)-2-butoxy-8-methoxy-9H-purin-6-amine

HRID 1666198Notes

Reaction equation

HRID 1666198 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][C:11]([O:15][CH3:16])=[N:12]2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4].[Br:18][CH2:19][CH2:20][CH:21](Br)C.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[Br:18][CH2:19][CH2:20][CH2:21][N:12]1[C:11]([O:15][CH3:16])=[N:10][C:9]2[C:13]1=[N:14][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[N:7][C:8]=2[NH2:17]

Participants

7

Reactant 4

HCID 962WaterHCID 78891,3-DibromobutaneHCID 11430Potassium CarbonateHCID 574571342-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine

Product 1

HCID 231584909-(3-Bromopropyl)-2-butoxy-8-methoxy-9H-purin-6-amineYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-butoxy-8-methoxyadenine (5 g, 14.2 mmol) in dimethylformamide (50 ml) were added 1,3-dibromobutane (7.2 ml) and potassium carbonate (9.2 g), and the mixture was stirred at room temperature for 1.5 hour. Water (200 ml) and ethyl acetate (75 ml) were added thereto, and the mixture was extracted, and further extracted with ethyl acetate (75 ml) twice. The organic layers were combined, dried over magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure. To the residue was added diethyl ether (25 ml), and the precipitated crystals were collected by filtration, washed with ether (5 ml), and dried to give the subtitle compound (3.6 g) as a white solid. Yield: 71%

Workup

  1. extractionthe mixture was extracted
  2. extractionfurther extracted with ethyl acetate (75 ml) twice
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo the residue was added diethyl ether (25 ml)
  7. filtrationthe precipitated crystals were collected by filtration
  8. washwashed with ether (5 ml)
  9. customdried

Sources & evidence

ORD record
ord-aeb930831a124e69ad5924a36ad1318d
Source dataset
uspto-grants-2011_10
Patent number
US08044056B2

Reaction notes

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