Potassium Carbonate → HCID 22928869, compound

HRID 1371465Notes

Reaction equation

HRID 1371465 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[Cl:16][C:17]1[N:25]=[C:24]2[C:20]([NH:21][CH:22]=[N:23]2)=[C:19]([NH2:26])[N:18]=1>CN(C=O)C>[Cl:16][C:17]1[N:25]=[C:24]2[C:20]([N:21]=[CH:22][N:23]2[CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[C:19]([NH2:26])[N:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 949042-Chloroadenine

Product 1

HCID 22928869HCID 22928869, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (1.1 g, 8 mmol) and 3-chloromethylpyridine hydrochloride (660 mg, 5 mmol) were added to a DMF solution (30 ml) comprising 2-chloroadenine (520 mg, 3 mmol), and the resultant was stirred while heating at 80° C. for 3 hours. The reaction solution was concentrated under reduced pressure, water was added thereto, and the precipitated solid was collected by filtration. Thus, 2-chloro-9-(3-pyridylmethyl)adenine was obtained (yield: 759 mg). Sodium (750 mg, 30 mmol) was added to butanol (50 ml), and the temperature of the mixture was raised to 90° C. to completely dissolve sodium therein. Subsequently, 2-chloro-9-(3-pyridylmethyl)adenine (430 mg, 1.5 mmol) was added thereto, and the resultant was heated under reflux for 2 hours. The solvent was concentrated under reduced pressure, water was added to the residue, and concentrated hydrochloric acid was added dropwise under ice cooling to neutralize the solution. Liquid separation was carried out with the addition of methylene chloride, and the organic layer was concentrated under reduced pressure. Acetic acid (30 ml) was added to the residue to dissolve it, bromine (660 mg, 5.5 mmol) was added thereto, and the resultant was allowed to react at room temperature all day and night. The reaction solution was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1). Thus, 310 mg of 8-bromo-2-butoxy-9-(3-pyridylmethyl)adenine was obtained. Subsequently, the title compound was obtained in the same manner as in Reference Example 3 and Example 1.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, water
  2. additionwas added
  3. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-74538f16164e4e42852fa3396901a1bb
Source dataset
uspto-grants-2007_01
Patent number
US07157465B2

Reaction notes

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