Dimethylformamide → 4-(Methylthio)furo[3,2-d]pyrimidine-6-carbaldehyde

HRID 32599Notes

Reaction equation

HRID 32599 reaction equation
C([Li])CCC.[CH3:6][S:7][C:8]1[C:9]2[O:16][CH:15]=[CH:14][C:10]=2[N:11]=[CH:12][N:13]=1.CN([CH:20]=[O:21])C.[Cl-].[NH4+]>C1COCC1>[CH3:6][S:7][C:8]1[C:9]2[O:16][C:15]([CH:20]=[O:21])=[CH:14][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 179657724-(Methylthio)furo[3,2-d]pyrimidine2×HCID 178418339Butyllithium

Product 1

HCID 179658684-(Methylthio)furo[3,2-d]pyrimidine-6-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Butyl lithium (as 1.6 M in hexanes, 7 mL) was added to a solution of 4-(methylthio)furo[3,2-d]pyrimidine (Intermediate 85) (1.21 g) in THF (25 mL) at −70° C. The reaction was stirred for 5 minutes, DMF (5 mL) added, and the reaction mixture allowed to warm to ambient temperature. 30% Saturated ammonium chloride solution (50 mL) was added and the mixture extracted into EtOAc (3×50 mL). The combined organics were washed with 50% saturated sodium carbonate solution (50 mL), water (50 mL), dried and the solvent removed to afford the title compound as a pale yellow solid (1.02 g) (the product contained 20% unreacted starting material but was used without further purification in subsequents steps);

Workup

  1. extractionthe mixture extracted into EtOAc (3×50 mL)
  2. washThe combined organics were washed with 50% saturated sodium carbonate solution (50 mL), water (50 mL)
  3. customdried
  4. customthe solvent removed

Sources & evidence

ORD record
ord-d2f7dc87311344098f3b7e5f54529e7e
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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