Sodium ethoxide → 5-(4-chlorobenzyl)-6-(3-chlorophenyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63926Notes

Reaction equation

HRID 63926 reaction equation
C([NH:9][C:10](=[O:37])[NH:11][C:12]1[O:13][C:14]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=2)=[C:15]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:16]=1[C:17](OCC)=[O:18])(=O)C1C=CC=CC=1.[O-]CC.[Na+]>CCO>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C:15]2[C:16]3[C:17](=[O:18])[NH:9][C:10](=[O:37])[NH:11][C:12]=3[O:13][C:14]=2[C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 118863090Ethyl 2-(3-benzoylureido)-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate

Product 1

HCID 1188631095-(4-chlorobenzyl)-6-(3-chlorophenyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 5,939.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(3-benzoylureido)-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate (53.6 mg, 0.1 mmol) in EtOH (2 mL) was added sodium ethoxide (13.6 mg, 0.2 mmol). The reaction was heated at 100° C. (MW) for 20 min, cooled to RT and quenched with aq. NH4Cl (2 mL). The reaction was concentrated to a residue which was diluted with water (3 mL) and extracted with EA (3×8 mL). The combined organic layers were dried over Na2SO4 and concentrated to give 5-(4-chlorobenzyl)-6-(3-chloro phenyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (2.3 g, 83% yield) as a white solid. 1H NMR (DMSO-d6) δ: 9.70 (brd s, 1H), 7.38 (m, 3H), 7.33 (d, J=8.5 Hz, 2H), 7.30-7.21 (m, 3H), 4.24 (s, 2H). LCMS: MH+ 387 and TR=2.685 min. Used without further purification.

Workup

  1. temperatureThe reaction was heated at 100° C. (MW) for 20 min
  2. customquenched with aq. NH4Cl (2 mL)
  3. concentrationThe reaction was concentrated to a residue which
  4. additionwas diluted with water (3 mL)
  5. extractionextracted with EA (3×8 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-abcd283634e24e3bb0f53572602d51d4
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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