Water → N9-(3-Azidopropyl)-2-amino-6-chloropurine

HRID 1695085Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8]([NH2:15])=[N:9][C:10]=2[Cl:14].[N-:16]=[N+:17]=[N-:18].[Na+].O>CS(C)=O>[N:16]([CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8]([NH2:15])=[N:9][C:10]=2[Cl:14])=[N+:17]=[N-:18]

Participants

Conditions

Temperature: 80 °C

Procedure

N9-(3-Chloropropyl)-2-amino-6-chlorpurine (21, 2.56 g, 10.40 mmol) and sodium azide (811 mg, 12.48 mmol) are dissolved in 25 mL DMSO and stirred at 80° C. for 16 h. After cooling to room temperature, the reaction mixture is poured into 150 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 the title compound as a colorless solid (650 mg, 2.57 mmol, 24%). 1H-NMR (400 MHz, DMSO-d6): δ=8.12 (s, 1H, H-8), 6.89 (s, 2H, NH2), 4.10 (t, J=6.8, 2H, CH2), 3.38 (t, J=6.8, 2H, CH2), 2.05 (m, 2H, CH2) ppm. MS (ESI) m/z 253.0 [M+H]+.

Workup

temperatureAfter cooling to room temperature
extractionextracted with CH2Cl2
washThe combined organic phases are washed with water
dry with materialdried over MgSO4
customevaporated in vacuo
customThe residue is purified by flash column chromatography (dichloromethane/methanol 50:1 to 10:1)

Sources & evidence

ORD record: ord-5f2dec05b2c64f169eaf727ba447898c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163479B2

Reaction notes

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