2,3-Dihydrofuran → HCID 12509180, compound

HRID 1065521Notes

Reaction equation

HRID 1065521 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][NH:3]1.[O:13]1[CH:17]=[CH:16][CH2:15][CH2:14]1>N1C=CC=CC=1>[O:13]1[CH2:14][CH2:15][CH2:16][CH:17]1[N:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:8])[N:7]([CH:14]2[CH2:15][CH2:16][CH2:17][O:13]2)[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 709342,3-DihydrofuranHCID 353768Methyl 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 12509180HCID 12509180, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 14 ml. of pyridine are dissolved 3.4 g. (20.0 mmoles) of methyl 1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carboxylate and 4.9 g. (70.0 mmoles) of 2,3-dihydrofuran and the solution is heated in a closed reaction vessel at 140° C. for 6 hours. The reaction mixture is then concentrated to dryness under reduced pressure and the residue is dissolved in 30 ml. of chloroform and applied to a column of 68 g. of silica gel. Elution is carried out with 250 ml. of chloroform and the eluate is concentrated to dryness under reduced pressure to give 0.8 g. (yield 12.9%) of methyl 1,3-bis(2-tetrahydrofuryl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carboxylate.

Workup

  1. concentrationThe reaction mixture is then concentrated to dryness under reduced pressure
  2. dissolutionthe residue is dissolved in 30 ml
  3. washElution
  4. concentrationof chloroform and the eluate is concentrated to dryness under reduced pressure
  5. customto give 0.8 g

Sources & evidence

ORD record
ord-3dbfefe6a35c4940ab3ee9df3f26c682
Source dataset
uspto-grants-1982_05
Patent number
US04329460

Reaction notes

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