Anisole → HCID 66739707, compound

HRID 1641505Notes

Reaction equation

HRID 1641505 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C1(OC)C=CC=CC=1.N(CC1C=CC(OC)=CC=1)=[N+]=[N-].[F:25][C:26]1[C:27](=[O:46])[NH:28][C:29](=[O:45])[N:30]([C@H:32]2[C@@H:35]([CH2:36][O:37]CC3C=CC=CC=3)[CH2:34][CH2:33]2)[CH:31]=1>CO>[F:25][C:26]1[C:27](=[O:46])[NH:28][C:29](=[O:45])[N:30]([C@H:32]2[C@@H:35]([CH2:36][OH:37])[CH2:34][CH2:33]2)[CH:31]=1

Participants

5

Reactant 3

HCID 7519Anisole2×HCID 6451240Aluminum(III) Chloride2×HCID 131727292HCID 131727292, compound

Product 1

HCID 66739707HCID 66739707, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In a 25 mL flask with AlCl3 (1.93 g, 14.4 mmol) inside, dry anisole 5 mL was added under argon to give a light yellow solution. In another flask with N3-PMB-5-fluoro-1-[cis-4-(benzyloxymethyl)cyclobutyl]uracil (0.66 g, 1.44 mmol) inside, dry anisole 5 mL was added, after which time AlCl3 solution was added to it ver slowly at room temperature. After addition finishes, the mixture was cooled to 0° C. and dry MeOH was added slowly to give a colorless solution at the end. Then the solvents were removed and the product was purified by silica gel flash chromatography (CH2Cl2: MeOH=20:1 to CH2Cl2: MeOH=10:1) to give a white solid (0.26 g, 74%, Rf=0.11 (CH2Cl2: MeOH=20:1)). 1H NMR (CD3OD, 400 MHz): δ IR (neat) νmax 3402, 3064, 2934, 1694, 1473, 1369, 1244, 1041, 1005, 913, 784, 706.

Workup

  1. customto give a light yellow solution
  2. additionAfter addition finishes
  3. customto give a colorless solution at the end
  4. customThen the solvents were removed
  5. customthe product was purified by silica gel flash chromatography (CH2Cl2: MeOH=20:1 to CH2Cl2: MeOH=10:1)
  6. customto give a white solid (0.26 g, 74%, Rf=0.11 (CH2Cl2: MeOH=20:1))

Sources & evidence

ORD record
ord-5ad7b1a7d8b841719b59d111930565d8
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

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