Methanol → 3-Hydroxy-7-methyl-2-(5-m-tolyl-[1,3,4]oxadiazol-2-yl)-pyrido[1,2-a]pyrimidin-4-one

HRID 536126Notes

Reaction equation

HRID 536126 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21]1[O:22][C:23]([C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)=[N:24][N:25]=1)C1C=CC=CC=1.C[Si](I)(C)C.N#N.CO>C(#N)C.O>[OH:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21]1[O:22][C:23]([C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)=[N:24][N:25]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 947NitrogenHCID 85247Trimethylsilyl iodideHCID 581010333-Benzyloxy-7-methyl-2-(5-m-tolyl-[1,3,4]oxadiazol-2-yl)-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 1359936133-Hydroxy-7-methyl-2-(5-m-tolyl-[1,3,4]oxadiazol-2-yl)-pyrido[1,2-a]pyrimidin-4-oneYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of the product from Example 8.4 (20 mg, 0.047 mmol) in acetonitrile (5 mL), was added trimethylsilyl iodide (54 uL, 0.38 mmol) dropwise under N2 at room temperature. After 2 h, methanol (5 mL) was added and the solution was stirred for 10 min. Water (10 mL) was added and the reaction extracted with dichloromethane. The organic phase was washed with aqueous sodium bisulfite solution, dried (Na2SO4) and concentrated in vacuo to afford the desired compound (88.6%).

Workup

  1. extractionthe reaction extracted with dichloromethane
  2. washThe organic phase was washed with aqueous sodium bisulfite solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4bdc230584d0436e95e2826632289ce4
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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