5-Fluorouracil → 1-[alpha-(2-Hydroxyethoxy)-4-methoxybenzyl]-5-fluorouracil

HRID 1649108Notes

Reaction equation

HRID 1649108 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.FC1C(=O)NC(=O)NC=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]2[O:39][CH2:38][CH2:37][O:36]2)=[CH:31][CH:30]=1.COC1C=CC(C=O)=CC=1>C(O)CO>[OH:39][CH2:38][CH2:37][O:36][CH:35]([N:10]1[CH:5]=[C:6]([F:17])[C:7](=[O:16])[NH:8][C:9]1=[O:11])[C:32]1[CH:31]=[CH:30][C:29]([O:28][CH3:27])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 33855-FluorouracilHCID 312444-MethoxybenzaldehydeHCID 2216272-(p-Methoxyphenyl)-1,3-dioxolaneHCID 68585259HCID 68585259, compound

Product 1

HCID 130571291-[alpha-(2-Hydroxyethoxy)-4-methoxybenzyl]-5-fluorouracil

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Bis-trimethylsilyl-5-fluorouracil prepared from 5-fluorouracil (10 g) as in Example 1 was reacted with 2-(4-methoxyphenyl)-1,3-dioxolan prepared from p-methoxybenzaldehyde and ethylene glycol, and treated as in Example 8 to give 6.5 g of crystalline 1-[α-(2-hydroxyethoxy)-4-methoxybenzyl]-5-fluorouracil.

Workup

  1. additiontreated as in Example 8

Sources & evidence

ORD record
ord-468deeef74404d3f854797d6f42e81a0
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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