Triacetoxyperiodinane → HCID 57732435, compound

HRID 1365068Notes

Reaction equation

HRID 1365068 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([F:22])=[C:12]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[OH:15])[CH:13]=2)[CH:5]=[CH:4][N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([F:22])=[C:12]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[CH:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57732438HCID 57732438, compound

Product 1

HCID 57732435HCID 57732435, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottomed flask was charged with [5-(2-amino-4-pyrimidinyl)-2-fluorophenyl]-(phenyl)methanol and dissolved in methylene chloride (10 mL). The resulting solution was treated with Dess-Martin periodinane and stirred at room temperature for 30 min. The reaction was quenched with a saturated solution of sodium bicarbonate, then the organic layer was removed, dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography to provide [5-(2-amino-4-pyrimidinyl)-2-fluorophenyl](phenyl)methanone (30 mg) as a white powder. H1 NMR (d6-dmso): 8.28-8.36 (m, 2H), 8.27 (dd, 1H), 7.79 (d, 2H), 7.70 (t, 1H), 7.56 (t, 2H), 7.50 (dd, 1H), 7.17 (d, 1H), 6.71 (br s, 2H). Mass (ES+)=294.1 (100%).

Workup

  1. customThe reaction was quenched with a saturated solution of sodium bicarbonate
  2. customthe organic layer was removed
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-06f5dfc0c96c4255ad352841ccf2743a
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

Loading…