Magnesium monoxide → Methyl thieno[2,3-d]pyrimidine-6-carboxylate

HRID 32516Notes

Reaction equation

HRID 32516 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[O-2].[Mg+2]>C(O)(C)C.[Pd]>[N:5]1[C:4]2[S:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:3]=2[CH:2]=[N:7][CH:6]=1

Participants

5

Reactant 2

HCID 6850729Magnesium monoxideHCID 17965841Methyl 4-chlorothieno[2,3-d]pyrimidine-6-carboxylate2×

Product 1

HCID 17965832Methyl thieno[2,3-d]pyrimidine-6-carboxylateYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

Methyl 4-chlorothieno[2,3-d]pyrimidine-6-carboxylate (intermediate 10) (114 mg), magnesium oxide (40 mg) and Pd/C (12 mg) in isopropanol (10 mL) were stirred under hydrogen for 48 hours. The solution was filtered through diatomaceous earth, washed with DCM (3×10 mL) and then concentrated in vacuo. Purification by flash chromatography on silica eluting with hexane:EtOAc (2:1) afforded the title compound as a white crystalline solid (76 mg, 78%);

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. washwashed with DCM (3×10 mL)
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica eluting with hexane:EtOAc (2:1)

Sources & evidence

ORD record
ord-25d917f38c5141bcaeeeb0b3d94bf05d
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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