Phosphorus oxychloride → HCID 22063733, compound

HRID 1828443Notes

Reaction equation

HRID 1828443 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:10]1[N:11]=[C:12]([NH:15][C:16]([C:18]2[CH:34]=[CH:33][N:21]3[C:22](=[O:32])[CH:23]=[C:24]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[N:25]=[C:20]3[CH:19]=2)=[O:17])[S:13][CH:14]=1)([CH3:9])([CH3:8])[CH3:7].[C:35](=O)([O-])[OH:36].[Na+]>CN(C)C=O>[C:6]([C:10]1[N:11]=[C:12]([NH:15][C:16]([C:18]2[CH:34]=[CH:33][N:21]3[C:22](=[O:32])[C:23]([CH:35]=[O:36])=[C:24]([N:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)[N:25]=[C:20]3[CH:19]=2)=[O:17])[S:13][CH:14]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 22063598HCID 22063598, compound

Product 1

HCID 22063733HCID 22063733, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Dimethylformamide (1 ml) was added dropwise with phosphorus oxychloride (66 μl, 0.712 mmol) under ice cooling, then warmed to room temperature, and stirred for 15 minutes. The reaction solution was cooled to 0° C. with ice, added with N8-[4-(tert-butyl)-1,3-thiazol-2-yl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidine-8-carboxamide (147 mg, 0.356 mmol) dissolved in dimethylformamide (4 ml) under ice cooling, and stirred at 0° C. for 2 hours and 30 minutes. The reaction solution was neutralized with saturated aqueous sodium hydrogencarbonate and concentrated under reduced pressure. The resulting residue was added with chloroform for extraction, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=40:1) to obtain 98.2 mg of the title compound as yellow crystals in a mixture with dimethylformamide.

Workup

  1. temperatureThe reaction solution was cooled to 0° C. with ice
  2. stirringstirred at 0° C. for 2 hours and 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. additionThe resulting residue was added with chloroform for extraction
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-03c3b32fc17e4d8b81997cf34de3074d
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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