Potassium Carbonate → N9-(3-Chloropropyl)-2-amino-6-chloropurine

HRID 1695084Notes

Reaction equation

HRID 1695084 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C([O-])([O-])=O.[K+].[K+].C[N:18](C=O)C.Br[CH2:23][CH2:24][CH2:25][Cl:26]>O>[Cl:26][CH2:25][CH2:24][CH2:23][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][C:9]([NH2:18])=[N:10][C:2]=2[Cl:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53592776-ChloropurineHCID 86615609DMF 1-bromo-3-chloropropane

Product 1

HCID 85823850N9-(3-Chloropropyl)-2-amino-6-chloropurineYield 36.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of 6-chloropurine (5.0 g, 29.48 mmol) and K2CO3 (4.48 g, 32.42 mmol) in dry DMF 1-bromo-3-chloropropane (13.92 g, 88.45 mmol) is added. The reaction mixture is heated to 50° C. for 1 min and stirred at room temperature for additional 3 h. The reaction mixture is poured into 120 mL of water and extracted with CH2Cl2. The combined organic phases are washed with water, dried over MgSO4 and evaporated in vacuo. The residue is purified by flash column chromatography (dichloromethane/methanol 50:1 to 10:1) to yield 2.6 g (10.65 mmol, 35%) of the title compound as a colorless solid. 1H-NMR (400 MHz, DMSO-d6): δ=8.11 (s, 1H, H-8), 6.91 (s, 2H, NH2), 4.16 (t, J=6.8, 2H, CH2), 3.63 (t, J=6.8, 2H CH2), 2.25 (m, 2H, CH2) ppm. MS (ESI) m/z 247.3 [M+H]+.

Workup

  1. additionis added
  2. extractionextracted with CH2Cl2
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue is purified by flash column chromatography (dichloromethane/methanol 50:1 to 10:1)

Sources & evidence

ORD record
ord-25928c8fa6354b1ca2f91a0da09e53cb
Source dataset
uspto-grants-2012_04
Patent number
US08163479B2

Reaction notes

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