5-Fluorouracil → 1-[alpha-(2-Acetoxyethoxy)-2-ethoxybenzyl]-5-fluorouracil

HRID 1649115Notes

Reaction equation

HRID 1649115 reaction equation
C[Si]([C:5]1[NH:10][C:9](=[O:11])[N:8]([Si](C)(C)C)[C:7](=[O:16])[C:6]=1[F:17])(C)C.F[C:19]1[C:20](=[O:26])NC(=O)NC=1.[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]1[O:40][CH2:39][CH2:38][O:37]1)[CH3:28].C(OC1C=CC=CC=1C=O)C>ClCCl.C(O)CO>[C:20]([O:37][CH2:38][CH2:39][O:40][CH:36]([N:10]1[CH:5]=[C:6]([F:17])[C:7](=[O:16])[NH:8][C:9]1=[O:11])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[O:29][CH2:27][CH3:28])(=[O:26])[CH3:19]

Participants

7

Reactant 4

HCID 33855-FluorouracilHCID 11950Benzaldehyde, 2-ethoxy-HCID 204806052-(2-Ethoxyphenyl)-1,3-dioxolanHCID 68585259HCID 68585259, compound

Product 1

HCID 132362561-[alpha-(2-Acetoxyethoxy)-2-ethoxybenzyl]-5-fluorouracil

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 6344DichloromethaneSolvent

Procedure

Bis(trimethylsilyl)5-fluorouracil prepared as in Example 1 from 5-fluorouracil (10 g), and 2-(2-ethoxyphenyl)-1,3-dioxolan (15 g) prepared from 2-ethoxybenzaldehyde and ethylene glycol were dissolved in dichloromethane (50 ml). The mixture was treated and acetylated as in Example 10 to give 6.2 g of crystalline 1-[α-(2-acetoxyethoxy)-2-ethoxybenzyl]-5-fluorouracil.

Workup

  1. additionThe mixture was treated

Sources & evidence

ORD record
ord-0fbd983164ec4a8a89ca6591addee897
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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