Sodium Bicarbonate → HCID 59717362, compound

HRID 75632Notes

Reaction equation

HRID 75632 reaction equation
[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11]([O:17][S:18]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)(=[O:20])=[O:19])=[CH:12][C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-])=O)[CH:29]=3)[C:5]2=[O:37])[CH2:3][CH2:2]1.C(=O)([O-])O.[Na+]>O1CCCC1>[NH2:34][C:30]1[CH:29]=[C:28]([N:6]2[C:7]3[N:14]([CH3:15])[C:13](=[O:16])[CH:12]=[C:11]([O:17][S:18]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:8]=3[C:9](=[O:10])[N:4]([CH:1]3[CH2:2][CH2:3]3)[C:5]2=[O:37])[CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59717031Toluene-4-sulfonic acid 3-cyclopropyl-8-methyl-1-(3-nitrophenyl)-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester

Product 1

HCID 59717362HCID 59717362, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of toluene-4-sulfonic acid 3-cyclopropyl-8-methyl-1-(3-nitrophenyl)-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 12 (21 g) obtained in Step 6 in tetrahydrofuran was added stannous chloride dihydrate (45 g), and the mixture was stirred at room temperature for 4 hrs. The reaction mixture was alkalified with saturated aqueous sodium hydrogen carbonate, an insoluble inorganic product was filtered off by suction using celite as a filtration aides, and the filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (chloroform:acetone=9:1) to give toluene-4-sulfonic acid 1-(3-aminophenyl)-3-cyclopropyl-8-methyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 13 (15 g, 74%) as a white solid.

Workup

  1. filtrationan insoluble inorganic product was filtered off by suction
  2. filtrationas a filtration aides
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (chloroform:acetone=9:1)

Sources & evidence

ORD record
ord-a13c58526b4b4befab836472b4ebfe73
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

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