Acetyl chloride → 2-Chloro-6-(2-propylimidazol-1-yl)purine

HRID 2264868Notes

Reaction equation

C(O[C@@H]1[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([Cl:36])=[N:23][C:24]=2[N:28]1[CH:32]=[CH:31][N:30]=[C:29]1[CH2:33][CH2:34][CH3:35])(=O)C.C(Cl)(C)=O>CC(O)=O>[Cl:36][C:22]1[N:21]=[C:20]2[C:25]([NH:26][CH:27]=[N:19]2)=[C:24]([N:28]2[CH:32]=[CH:31][N:30]=[C:29]2[CH2:33][CH2:34][CH3:35])[N:23]=1

Participants

Conditions

Temperature: 65 °C

Procedure

9-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-2-chloro-6-(2-propylimidazol-1-yl)purine (4.99 g, 9.6 mmol) was dissolved in HOAc (400 mL). To the solution was added AcCl (4.0 mL, 4.42 g, 56.3 mmol), and the mixture was stirred at 65° C. for 1.5 h in a sealed flask (reaction almost complete, TLC). Volatiles were evaporated in vacuo, and the residue was washed (CH2Cl2), and dissolved in 0.1 N NaOH/H2O. Precipitation with CO2 gave 2-chloro-6-(2-propylimidazol-1-yl)purine (2.20 g, 88%). Recrystallization (MeOH) gave the pure material (1.93 g, 77%).

Workup

customreaction almost complete
customVolatiles were evaporated in vacuo
washthe residue was washed (CH2Cl2)
dissolutiondissolved in 0.1 N NaOH/H2O
customPrecipitation with CO2

Sources & evidence

ORD record: ord-dcb49abe1f6b4eedae72d2eeb746e494
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855285B2

Reaction notes

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