Triacetoxyperiodinane → 2-[3-Phenyl-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 33975Notes

Reaction equation

HRID 33975 reaction equation
[OH:1][CH:2]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:3][NH:4][C:5]1[N:10]([CH3:11])[C:9](=[O:12])[C:8]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[C:7]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[N:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.ClCCl.CO.[2H]C([2H])([2H])C#N.[2H]O[2H]>C(#N)C.ClCCl>[CH3:11][N:10]1[C:9](=[O:12])[C:8]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[C:7]([C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)[N:6]=[C:5]1[NH:4][CH2:3][C:2](=[O:1])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 159087Triacetoxyperiodinane2×HCID 116626342-(2-Hydroxy-3-phenyl-propylamino)-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-oneHCID 21226129Dichloromethane methanolHCID 131725767CD3CN D2O

Product 1

HCID 115109142-[3-Phenyl-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a striring suspension of 2-(2-hydroxy-3-phenyl-propylamino)-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (150 mg, 0.32 mmol) in 5 mL dry acetonitrile and 5 mL dichloromethane was added Dess-Martin Periodinane (206 mg, 0.49 mmol). The reaction mixture turned to an orange color within 3 min. After 30 min, TLC (95:5 dichloromethane/methanol) showed approximately 15% of the starting material remained. More Dess-Martin Periodinane (50 mg, 0.12 mmol) was added and the reaction was stirred for and additional 30 min. The curde product was purified on 10 g silica eluting with 0 to 3% methanol/dichloromethane to give a clear film. The material was further purified on reverse phase high performance chromatography eluting with water/acetonitrile (0.1% TFA) gradient. The final material was lyophilized from 50% acetonitrile/water to give a pale yellow powder. M+1=461.3. NMR (CD3CN/D2O 3:1) s (3H; 3.5 ppm), s (2H; 3.8 ppm), s (2H; 4.3 ppm), dd (2H; 7.15 ppm), m (4H, 7.2-7.3 ppm), m (3H, 7.45-7.55 ppm), d (2H, 7.62 ppm), d (1H, 7.72 ppm), d (1H, 7.84 ppm), d (1H, 7.88 ppm), d (2H, 8.39 ppm). M+1=461.2.

Workup

  1. waitAfter 30 min
  2. customThe curde product was purified on 10 g silica eluting with 0 to 3% methanol/dichloromethane
  3. customto give a clear film
  4. customThe material was further purified on reverse phase high performance chromatography
  5. washeluting with water/acetonitrile (0.1% TFA) gradient
  6. customto give a pale yellow powder

Sources & evidence

ORD record
ord-7605003714b54687958581c644bd64d5
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

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