Toluene → HCID 178434859, compound

HRID 2191536Notes

Reaction equation

HRID 2191536 reaction equation
[CH3:1][CH:2]1[CH:6]([C:7]([O:9]C)=O)[C:5](=O)[CH2:4][O:3]1.[CH:12]([NH2:14])=[NH:13].C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][CH:2]1[C:6]2[C:7]([OH:9])=[N:14][CH:12]=[N:13][C:5]=2[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 68047FormamidineHCID 332983METHYL 2-METHYL-4-OXO-OXOLANE-3-CARBOXYLATE

Product 1

HCID 178434859HCID 178434859, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 2-methyl-4-oxotetrahydrofuran-3-carboxylate (8.3 g, 52.8 mmol), formamidine (7.0 g, 68.6 mmol) and toluene (200 mL) was heated to reflux under Dean-Stark conditions overnight. The mixture was allowed to cool to room temperature, diluted with water and neutralized by the addition of saturated Na2CO3. The organic layer was separated and the aqueous layer extracted with EtOAc (5×200 mL). The combined organic layers were dried with brine, MgSO4 and concentrated. The residue was purified by column chromatography (100% EtOAc to 5% MeOH:EtOAc) to give 5-methyl-5,7-dihydrofuro[3,4-d]pyrimidin-4-ol as a brown solid. 1H NMR (DMSO-d6, 400 MHz) δ 12.58 (s, 1H), 8.18 (s, 1H), 5.18 (bs, 1H), 4.82 (d, J=14.4 Hz, 1H), 4.72 (d, J=14.4 Hz, 1H), 1.37 (d, J=6.8 Hz, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under Dean-Stark conditions overnight
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with EtOAc (5×200 mL)
  5. dry with materialThe combined organic layers were dried with brine, MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (100% EtOAc to 5% MeOH:EtOAc)

Sources & evidence

ORD record
ord-4a66c57e510e4513a97ae75500d2a4ce
Source dataset
uspto-grants-2012_12
Patent number
US08329701B2

Reaction notes

Loading…