Sodium Carbonate → 2-Methanesulfonyl-thieno[2,3-h]quinazoline-8-carboxylic acid tert-butyl ester

HRID 908333Notes

Reaction equation

HRID 908333 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:22][C:11]2=[CH:12][CH:13]=[C:14]3[C:19]([N:18]=[C:17](SC)[N:16]=[CH:15]3)=[C:10]2[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:24]1C=CC=C(C(OO)=O)C=1.C([O-])([O-])=O.[Na+].[Na+].[O-:40][S:41]([O-:44])(=S)=O.[Na+].[Na+]>C(Cl)Cl.[Cl-].[Na+].O.CC(C)=O>[C:1]([O:5][C:6]([C:8]1[S:22][C:11]2=[CH:12][CH:13]=[C:14]3[C:19]([N:18]=[C:17]([S:41]([CH3:24])(=[O:44])=[O:40])[N:16]=[CH:15]3)=[C:10]2[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 592627012-Methylsulfanyl-thieno[2,3-h]quinazoline-8-carboxylic acid tert-butyl ester

Product 1

HCID 592629202-Methanesulfonyl-thieno[2,3-h]quinazoline-8-carboxylic acid tert-butyl esterYield 88%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Methylsulfanyl-thieno[2,3-h]quinazoline-8-carboxylic acid tert-butyl ester (6.50 g, 19.55 mmol) was suspended/dissolved in DCM (150 mL) and cooled in an ice-bath. 3-chloroperbenzoic acid (22.49 g, 97.76 mmol, ˜75% pure) was added in one portion and the resultant suspension was stirred at 0° C. for 5 minutes and at room temperature for a further 55 minutes. This mixture was then carefully added to a 1:1:1 mixture of saturated Na2CO3, saturated Na2S2O3 and brine (˜500 mL). The organic layer was separated and the aqueous layer was further extracted with DCM (3×200 mL). The combined organics were washed with brine (1×100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The yellow solid obtained was redissolved in acetone, silica (˜80 mL) was added and the suspension was concentrated under reduced pressure. The solid obtained was subjected to column chromatography (gradient elution, 5-10% EtOAc in DCM, ˜600 mL silica) to give a yellow solid (6.25 g, 88% yield). MS (ES+) 365. δH (CDCl3) 1.7 (9H, s), 3.5-3.6 (3H, s), 8.0 (1H, d), 8.2 (1H, d), 8.9 (1H, s), 9.6 (1H, s)

Workup

  1. temperaturecooled in an ice-bath
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was further extracted with DCM (3×200 mL)
  4. washThe combined organics were washed with brine (1×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe yellow solid obtained
  9. additionsilica (˜80 mL) was added
  10. concentrationthe suspension was concentrated under reduced pressure
  11. customThe solid obtained
  12. washwas subjected to column chromatography (gradient elution, 5-10% EtOAc in DCM, ˜600 mL silica)

Sources & evidence

ORD record
ord-46ee15de3e17444aa80fc8c580e9265b
Source dataset
uspto-grants-2011_09
Patent number
US08017619B2

Reaction notes

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