5-Fluorouracil → 1-[alpha-(2-Hydroxyethoxy)-3,4,5-trimethoxybenzyl]-5-fluorouracil

HRID 1649113Notes

Reaction equation

HRID 1649113 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].COC1C=C(C=C(OC)C=1OC)C=O.C[Si]([C:36]1[NH:41][C:40](=[O:42])[N:39]([Si](C)(C)C)[C:38](=[O:47])[C:37]=1[F:48])(C)C.FC1C(=O)NC(=O)NC=1>ClCCl.C(O)CO>[OH:14][CH2:15][CH2:16][O:17][CH:13]([N:41]1[CH:36]=[C:37]([F:48])[C:38](=[O:47])[NH:39][C:40]1=[O:42])[C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

7

Reactant 4

HCID 33855-FluorouracilHCID 68583,4,5-TrimethoxybenzaldehydeHCID 131241962-(3,4,5-Trimethoxyphenyl)-1,3-dioxolaneHCID 68585259HCID 68585259, compound

Product 1

HCID 155835561-[alpha-(2-Hydroxyethoxy)-3,4,5-trimethoxybenzyl]-5-fluorouracil

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 6344DichloromethaneSolvent

Procedure

2-(3,4,5-Trimethoxyphenyl)-1,3-dioxolan (20.3 g) prepared from 3,4,5-trimethoxybenzaldehyde and ethylene glycol was dissolved in dichloromethane (50 ml). To the solution bis(trimethylsilyl)-5-fluorouracil prepared from 5-fluorouracil (10 g) was added and treated as in Example 10 to give 7.2 g of crystalline 1-[α-(2-hydroxyethoxy)-3,4,5-trimethoxybenzyl]-5-fluorouracil.

Workup

  1. additionwas added
  2. additiontreated as in Example 10

Sources & evidence

ORD record
ord-29b421abb45d414cbb44ab7d76d30dcb
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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