Sodium Carbonate → 4-(Methylthio)furo[3,2-d]pyrimidine

HRID 32598Notes

Reaction equation

HRID 32598 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[C:6]2[O:13][CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC#N>[CH3:1][S:2][C:5]1[C:6]2[O:13][CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 4378561Sodium methanethiolateHCID 179658524-Chlorofuro(3,2-d)pyrimidine2×

Product 1

HCID 179657724-(Methylthio)furo[3,2-d]pyrimidineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Sodium thiomethoxide (1.2 g) was added to a solution of 4-chlorofuro[3,2-d]pyrimidine (Intermediate 84) (1.32 g) in MeCN (100 mL). The mixture was heated to 90° C. for 60 minutes, cooled, and added to 50% sodium carbonate solution (100 ml). The resulting mixture was extracted into EtOAc (3×100 mL). The combined organics were dried (MgSO4) and the solvent removed to afford the title compound as a pale orange solid (1.21 g, 85%);

Workup

  1. temperaturecooled
  2. extractionThe resulting mixture was extracted into EtOAc (3×100 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. customthe solvent removed

Sources & evidence

ORD record
ord-54ce7f0e76c1424980548c1c60d9d36a
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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