Hydrochloric Acid → HCID 178450379, compound

HRID 2111662Notes

Reaction equation

HRID 2111662 reaction equation
Cl.[CH2:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([NH:11][C:12](Br)([OH:25])[N:13]2[CH2:16][C:17]2[CH:18]=[N:19][C:20]([Cl:24])=[C:21]([Cl:23])[CH:22]=2)=[C:9]([NH2:27])[N:8]=1)[CH2:3][CH2:4][CH3:5]>C(O)CCC>[CH2:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([OH:25])[N:13]2[CH2:16][C:17]2[CH:18]=[N:19][C:20]([Cl:24])=[C:21]([Cl:23])[CH:22]=2)=[C:9]([NH2:27])[N:8]=1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86593356HCID 86593356, compound

Product 1

HCID 178450379HCID 178450379, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Concentrated hydrochloric acid (4 ml) was added to a butanol suspension (4 ml) comprising 2-n-butoxy-8-bromo-9-(5,6-dichloro-3-pyridylmethyl)-8-hydroxyadenine (150 mg, 0.34 mmol) obtained in the same manner as in Reference Example 2, and the resultant was allowed to react at 70° C. for 9 hours. The reaction solution was concentrated under reduced pressure, water (30 ml) was added to the residue under ice cooling, and the solution was neutralized with an aqueous solution of 1N sodium hydroxide. The precipitated solid was collected by filtration, crude crystal was purified by silica gel column chromatography (methylene chloride:methanol=25:1), and 45 mg of the title compound was obtained as a white powdery crystal (yield: 35%).

Workup

  1. customobtained in the same manner as in Reference Example 2
  2. customto react at 70° C. for 9 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure, water (30 ml)
  4. additionwas added to the residue under ice cooling
  5. filtrationThe precipitated solid was collected by filtration
  6. customcrude crystal was purified by silica gel column chromatography (methylene chloride:methanol=25:1)

Sources & evidence

ORD record
ord-db1816aca3e949628c48d1d36d64b63e
Source dataset
uspto-grants-2009_04
Patent number
US07521454B2

Reaction notes

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