Triacetoxyperiodinane → 2-[3-(4-Methoxy-phenyl)-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 33970Notes

Reaction equation

HRID 33970 reaction equation
[OH:1][CH:2]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[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>[CH3:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][C:2](=[O:1])[CH2:3][NH:4][C:5]2[N:10]([CH3:11])[C:9](=[O:12])[C:8]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=3)=[C:7]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[N:6]=2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 597965072-[2-Hydroxy-3-(4-methoxy-phenyl)-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Product 1

HCID 112488622-[3-(4-Methoxy-phenyl)-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 2-[2-hydroxy-3-(4-methoxy-phenyl)-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (765 mg, 1.55 mmol) in 20 mL dichloromethane was added Dess-Martin Periodinane (660 mg, 1.55 mmol). The dark red solution was stirred for 18 h at room temperature. The reaction mixture was diluted with 80 mL dichloromethane and washed twice with 15 mL 5% sodium bicarbonate, and dried over magnesium sulfate. The product was purified on 40 g silica eluting with 0 to 4% methanol/dichloromethane to provide the product as a yellow foam. The product was further purified on reverse phase high performance chromatography using an water/acetonitrile (0.1% TFA) gradient. The final sample was lyophilized from 50% acetonitrile/water to give a yellow powder. M+1=491.2.

Workup

  1. washwashed twice with 15 mL 5% sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. customThe product was purified on 40 g silica eluting with 0 to 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-8f7440757fdb4dfa9618d74a2622bfc2
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

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