1-Butanol → HCID 22928937, compound

HRID 1371466Notes

Reaction equation

HRID 1371466 reaction equation
[Na].Cl[C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[C:5]([NH2:19])[N:4]=1.[Br:20]Br.[CH2:22]([OH:26])[CH2:23][CH2:24][CH3:25]>>[Br:20][C:8]1[N:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:10]2[C:6]([N:7]=1)=[C:5]([NH2:19])[N:4]=[C:3]([O:26][CH2:22][CH2:23][CH2:24][CH3:25])[N:11]=2

Participants

5

Reactant 4

HCID 2631-ButanolHCID 24408BromineHCID 5360545Sodium2×HCID 22928869HCID 22928869, compound

Product 1

HCID 22928937HCID 22928937, compound

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. temperaturethe resultant was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe solvent was concentrated under reduced pressure, water
  4. additionwas added to the residue, and concentrated hydrochloric acid
  5. additionwas added dropwise under ice cooling
  6. customLiquid separation
  7. additionwas carried out with the addition of methylene chloride
  8. concentrationthe organic layer was concentrated under reduced pressure
  9. additionAcetic acid (30 ml) was added to the residue
  10. additionwas added
  11. customto react at room temperature all day and night
  12. customThe reaction solution was removed by distillation under reduced pressure
  13. customthe residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-d432b7ee5852492aa701a0ea6538901f
Source dataset
uspto-grants-2007_01
Patent number
US07157465B2

Reaction notes

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