Anisole → HCID 68851738, compound

HRID 1727318Notes

Reaction equation

HRID 1727318 reaction equation
C([O:8][CH2:9][C@@H:10]1[C@H:13]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][CH:17]=[N:18][C:19]=3[NH2:23])[CH2:12][CH2:11]1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>CO>[OH:8][CH2:9][C@@H:10]1[C@H:13]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][CH:17]=[N:18][C:19]=3[NH2:23])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 7519Anisole2×HCID 6451240Aluminum(III) ChlorideHCID 66739673HCID 66739673, compound

Product 1

HCID 68851738HCID 68851738, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 50 mL flask with 9-[cis-4-(benzyloxymethyl)-cyclobutyl]adenine (63.2 mg, 0.2 mmol) inside, dry anisole 5 mL was added to give a light yellow solution under argon. In another 10 mL flask with AlCl3 inside, dry anisole 2 mL was added under argon to give a totally clear red solution. This solution was added drop by drop to the first flask to give a red solution. After stirring at ambient temperature for 1 hr, TLC showed no starting material. The reaction mixture was cooled to 0° C. and dry MeOH was added drop by drop until the red color disappeared. The solvents were removed by rotovap to give an off-white solid and this was purified by silica gel flash chromatography (CH2Cl2:MeOH=15:1) to yield a white solid (33 mg, 72.4%, Rf=0.15 (CH2Cl2:MeOH=15:1)).

Workup

  1. customto give a light yellow solution under argon
  2. customto give a totally clear red solution
  3. additionThis solution was added drop by drop to the first flask
  4. customto give a red solution
  5. temperatureThe reaction mixture was cooled to 0° C.
  6. customThe solvents were removed by rotovap
  7. customto give an off-white solid
  8. customthis was purified by silica gel flash chromatography (CH2Cl2:MeOH=15:1)
  9. customto yield a white solid (33 mg, 72.4%, Rf=0.15 (CH2Cl2:MeOH=15:1))

Sources & evidence

ORD record
ord-f27ce29aec7840d094bf8fb2a129305f
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

Loading…