Sodium Thiosulfate → tert-Butyl 2-(methanesulfonyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 352881Notes

Reaction equation

HRID 352881 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13](SC)[N:14]=[CH:15][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:21]1C=CC=C(C(OO)=O)C=1.[S:31]([O-:35])([O-])(=[O:33])=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([S:31]([CH3:21])(=[O:35])=[O:33])[N:14]=[CH:15][C:10]=2[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22710609HCID 22710609, compound

Product 1

HCID 22709841tert-Butyl 2-(methanesulfonyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(tert-butoxycarbonyl)-2-methylthio-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (2.20 g) in methylene chloride (80 ml) was added metachloroperbenzoic acid (3.37 g). After stirring for 4 hours, a 10% aqueous solution (100 ml) of sodium thiosulfate and a saturated aqueous solution (100 ml) of sodium bicarbonate were added to the reaction mixture and the mixture was separated into layers. The water layer was extracted with methylene chloride (2×50 ml). The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:acetone=20:1→10:1), whereby the title compound (2.34 g) was obtained as a colorless solid.

Workup

  1. customthe mixture was separated into layers
  2. extractionThe water layer was extracted with methylene chloride (2×50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column (methylene chloride:acetone=20:1→10:1), whereby the title compound (2.34 g)
  7. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-f229fac0d5ed4a128a5a33adf98a90c3
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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