Nitrogen → 2-Methanesulfonyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 1694850Notes

Reaction equation

HRID 1694850 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:18][C:8]2[N:9]=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[N:11]=[C:12](Cl)[C:7]=2[CH:6]=1)=[O:4].N#N>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:18][C:8]2[N:9]=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 947NitrogenHCID 593764254-Chloro-2-methanesulfonyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Product 1

HCID 593764492-Methanesulfonyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-2-methanesulfonyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (700 mg, 2.2 mmol) in THF/MeOH (10/10 mL) purged with N2 was added Pd/C (700 mg). The reaction mixture was purged with N2, evacuated and purged with H2 three times. After 6 h, the mixture was filtered via Celite and concentrated. The residue dissolved in MeOH/CH2Cl2 and the solid was filtered. The filtrate containing the product was concentrated and used without further purification. ESIMS calcd 273 (M++H), found 273 (M++H).

Workup

  1. customThe reaction mixture was purged with N2
  2. customevacuated
  3. custompurged with H2 three times
  4. filtrationthe mixture was filtered via Celite
  5. concentrationconcentrated
  6. dissolutionThe residue dissolved in MeOH/CH2Cl2
  7. filtrationthe solid was filtered
  8. additionThe filtrate containing the product
  9. concentrationwas concentrated
  10. customused without further purification

Sources & evidence

ORD record
ord-75b327c996ab4bf1b52953676a138120
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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