1-Bromo-3-chloropropane → 9-(3-Chloropropyl)-2-butoxy-8-methoxy-9H-purin-6-amine

HRID 590424Notes

Reaction equation

HRID 590424 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][Cl:35]>CN(C=O)C>[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][CH2:34][Cl:35])=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178450370HCID 178450370, compound

Product 1

HCID 592526379-(3-Chloropropyl)-2-butoxy-8-methoxy-9H-purin-6-amineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine trifluoroacetate (4.7 g, 13.38 mmol) and potassium carbonate (4.62 g, 33.4 mmol) in dry DMF (50 ml) were stirred and heated at 50° C., under nitrogen, for 75 mins. The mixture was allowed to cool to room temperature and then cooled to 0° C. and 1-bromo-3-chloropropane (2.106 g, 13.38 mmol) was added. The mixture was stirred at 0 to 10° C. for approximately 5 hours then allowed to warm to room temperature and stirred for approximately a further 40 hours when LCMS indicated approximately 70% of the desired product.

Workup

  1. temperatureto cool to room temperature
  2. temperaturecooled to 0° C.
  3. temperatureto warm to room temperature
  4. stirringstirred for approximately a further 40 hours when LCMS

Sources & evidence

ORD record
ord-b3a34ab320ab441db4e35d8d2098af3f
Source dataset
uspto-grants-2016_01
Patent number
US09233962B2

Reaction notes

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