2,3-Dihydrofuran → HCID 12890669, compound

HRID 1065520Notes

Reaction equation

HRID 1065520 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][NH:3]1.[O:14]1[CH:18]=[CH:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[O:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[N:3]1[CH:4]=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6](=[O:8])[NH:7][C:2]1=[O:1]

Participants

4

Reactant 2

HCID 709342,3-DihydrofuranHCID 1014115-Carbethoxyuracil

Product 1

HCID 12890669HCID 12890669, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5.52 g. (30 mmoles) of ethyl 1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carboxylate, 15 g. of 2,3-dihydrofuran and 15 ml. of pyridine is heated at 135° C. for 6 hours. The reaction mixture is concentrated to dryness under reduced pressure and, with the addition of 20 ml. of water, the pyridine is azeotropically removed. The residue is dissolved in 50 ml. of 50% ethanol and heated at 75° C. for 2 hours. The reaction mixture is concentrated to dryness under reduced pressure and the residue is stirred well with 40 ml. of chloroform. Then, 0.9 g. of insoluble ethyl 1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carboxylate is recovered. The mother liquor is concentrated to dryness and the residue is recrystallized from 15 ml. of ethanol to give 3.1 g. (yield: 40.6%) of ethyl 1-(2-tetrahydrofuryl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carboxylate, melting point: 125° C.

Workup

  1. additionA mixture of 5.52 g
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure and, with the addition of 20 ml
  3. customof water, the pyridine is azeotropically removed
  4. dissolutionThe residue is dissolved in 50 ml
  5. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  6. customof insoluble ethyl 1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carboxylate is recovered
  7. concentrationThe mother liquor is concentrated to dryness
  8. customthe residue is recrystallized from 15 ml
  9. customof ethanol to give 3.1 g

Sources & evidence

ORD record
ord-9a5dd5f82bcb473c81e25eb35f5be841
Source dataset
uspto-grants-1982_05
Patent number
US04329460

Reaction notes

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