Triacetoxyperiodinane → HCID 11656333, compound

HRID 33979Notes

Reaction equation

HRID 33979 reaction equation
[OH:1][CH:2]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:3][N:4]1[C:9]2=[N:10][C:11]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[C:13](=[O:14])[N:8]2[CH2:7][CH2:6][CH2:5]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:3][N:4]1[C:9]2=[N:10][C:11]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[C:13](=[O:14])[N:8]2[CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59796517HCID 59796517, compound

Product 1

HCID 11656333HCID 11656333, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9-(2-hydroxy-3-phenyl-propyl)-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (50 mg, 0.1 mmol) in CH2Cl2 (5 mL) was treated with the Dess Martin Periodinane (450 mg, 1.1 mmol). After the mixture was stirred at room temperature for 5 hr, the mixture was washed with NaHCO3 (aq). The organic residue was loaded to a silica column and eluted with 0-4% (2N NH3-MeOH)/CH2Cl2. The product (4) was collected as a yellow solid (35 mg, 70%). M+1 505.

Workup

  1. washthe mixture was washed with NaHCO3 (aq)
  2. washeluted with 0-4% (2N NH3-MeOH)/CH2Cl2
  3. customThe product (4) was collected as a yellow solid (35 mg, 70%)

Sources & evidence

ORD record
ord-f1563883810847feb9a5da2ef4edf33e
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

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