Dichloromethane → Furo(3,2-d)pyrimidin-4-ol

HRID 32596Notes

Reaction equation

HRID 32596 reaction equation
[NH2:1][C:2]([C:4]1[O:5][CH:6]=[CH:7][C:8]=1[NH:9][C:10](=O)OC(C)(C)C)=[O:3].C(Cl)Cl>CN(C=O)C>[N:9]1[C:8]2[CH:7]=[CH:6][O:5][C:4]=2[C:2](=[O:3])[NH:1][CH:10]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 53439236tert-Butyl (2-carbamoylfuran-3-yl)carbamate2×

Product 1

HCID 135667605Furo(3,2-d)pyrimidin-4-olYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 2-(aminocarbonyl)-3-furylcarbamate (Intermediate 82) (3.38 g) was stirred in DMF (25 mL) and DCM (25 mL) for 30 minutes. The solvent was removed and the crude product was heated at 80° C. in triethylorthoformate (20 mL) for 30 minutes. The mixture was cooled, poured into ether (100 mL) collected by filtration and washed with ether to afford a first crop of the title compound as a pale yellow solid (1.31 g, 65%). The filtrate was evaporated and triturated with EtOAc to afford a further crop (296 mg, 15%);

Workup

  1. customThe solvent was removed
  2. temperatureThe mixture was cooled
  3. additionpoured into ether (100 mL)
  4. filtrationcollected by filtration
  5. washwashed with ether

Sources & evidence

ORD record
ord-c4a8ce2ccd224a12be2294839c6a973c
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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