5-Fluorouracil → 1-(2, 4-Dimethoxycyclohexylcarbamoyl)-5-fluorouracil

HRID 615150Notes

Reaction equation

HRID 615150 reaction equation
COC1CC(OC)CCC1N.COC1C=C(OC)C=CC=1N.[H][H].C(Cl)(Cl)=O.[CH3:29][O:30][CH:31]1[CH2:36][CH:35]([O:37][CH3:38])[CH2:34][CH2:33][CH:32]1[N:39]=[C:40]=[O:41].[N-]=C=O.[F:45][C:46]1[C:47](=[O:53])[NH:48][C:49](=[O:52])[NH:50][CH:51]=1>[Ru]=O.CO.N1C=CC=CC=1>[CH3:29][O:30][CH:31]1[CH2:36][CH:35]([O:37][CH3:38])[CH2:34][CH2:33][CH:32]1[NH:39][C:40]([N:50]1[CH:51]=[C:46]([F:45])[C:47](=[O:53])[NH:48][C:49]1=[O:52])=[O:41]

Participants

11

Reactant 7

HCID 33855-FluorouracilHCID 6371PhosgeneHCID 176522,4-DimethoxyanilineHCID 105034IsocyanateHCID 451221212,4-Dimethoxycyclohexan-1-amineHCID 540156612, 4-DimethoxycyclohexylisocyanateHCID 178418361HCID 178418361, compound

Product 1

HCID 106390511-(2, 4-Dimethoxycyclohexylcarbamoyl)-5-fluorouracil

Reagents, catalysts & solvents 3

HCID 178527103HCID 178527103, compoundCatalystHCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

The 2, 4-dimethoxycyclohexylamine reduced from 2, 4-dimethoxyaniline by hydrogen at 110 atmospheres over a ruthenium oxide catalyst in methanol was treated with phosgene and 2, 4-dimethoxycyclohexylisocyanate was synthesized. This isocyanate, 9.2 g, was allowed to react with 6.8 g of 5-fluorouracil in 30 ml of pyridine at 90° C. for 2 hr. After evaporating the pyridine, the residue was chromatographed on silica gel and two kinds of isomers, 3.2 and 2.8 g respectively, of 1-(2, 4-dimethoxycyclohexylcarbamoyl)-5-fluorouracil were obtained. Their melting points were 122°-125° C. (Compound No. 10) and 128°-130° C. (Compound No. 11), respectively. NMR: 0.7-2.50 (6H b CH2) 2.65 (H s NHCH) 3.58 (6H s OCH3) 4.10-4.51 (H s CHOCH3) 8.38 (H d C6 --H) 9.50 (H d NHCO) 12.25 (H b N3 --H).

Workup

  1. customwas synthesized
  2. customAfter evaporating the pyridine
  3. customthe residue was chromatographed on silica gel and two kinds of isomers, 3.2 and 2.8 g respectively

Sources & evidence

ORD record
ord-8f45c7a16a9e4309943781b439cf8d2b
Source dataset
uspto-grants-1985_02
Patent number
US04497815

Reaction notes

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