Pyridine → HCID 15583553, compound

HRID 1649109Notes

Reaction equation

HRID 1649109 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH:5]([N:15]1[CH:22]=[C:21]([F:23])[C:19](=[O:20])[NH:18][C:16]1=[O:17])[C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:13][O:14][C:8]=2[CH:7]=1.N1C=CC=CC=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[C:30]([O:1][CH2:2][CH2:3][O:4][CH:5]([N:15]1[CH:22]=[C:21]([F:23])[C:19](=[O:20])[NH:18][C:16]1=[O:17])[C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:13][O:14][C:8]=2[CH:7]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13057130HCID 13057130, compound

Product 1

HCID 15583553HCID 15583553, compound

Procedure

1-[α-(2-Hydroxyethoxy)-3,4-methylendioxybenzyl]-5-fluorouracil obtained in Example 10 was dissolved in acetic anhydride (20 ml) and pyridine (20 ml) followed by stirring at room temperature for 3 hours. The reaction mixture was poured into ice-water and the resulting oil was extracted with chloroform (100 ml). The extract was washed with hydrochloric acid and then water, dried over magnesium sulfate and evaporated under reduced pressure to remove chloroform. The residue was treated with ligroinacetone to give 4.3 g of crystalline 1-[α-(2-acetoxyethoxy)-3,4-methylenedioxybenzyl]-5-fluorouracil.

Workup

  1. extractionthe resulting oil was extracted with chloroform (100 ml)
  2. washThe extract was washed with hydrochloric acid
  3. dry with materialwater, dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove chloroform
  6. additionThe residue was treated with ligroinacetone

Sources & evidence

ORD record
ord-96b7a049baf544cdb6b089ae016f1814
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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