Trimethylamine → HCID 10665745, compound

HRID 615147Notes

Reaction equation

HRID 615147 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:10](Cl)(Cl)=[O:11].[CH3:14][O:15][C:16]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].CN(C)C>N1C=CC=CC=1>[CH3:14][O:15][C:16]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[CH:20][C:17]=1[CH2:18][NH:19][C:10]([N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])=[O:11]

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 33855-FluorouracilHCID 6371PhosgeneHCID 3892112,3,4-Trimethoxybenzylamine

Product 1

HCID 10665745HCID 10665745, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

5-Fluorouracil, 3.9 g, was dissolved in 80 ml of pyridine, the solution was cooled to 5° C., and 4 g of phosgene was blown into it. After stirring at 20° C. for 2 hr, the solution was cooled to 5° C., 5.8 g of 2, 3, 4-trimethoxybenzylamine and 3 ml of trimethylamine were gradually added to it, and the temperature was raised to 20° C. in 2 hr. After removing precipitate, pyridine was evaporated from the solution. Hydrochloric acid water and dichloromethane were added to the remainder. The solution was shaked, the dichloromethane layer was evaporated, the residue was recrystallized from methanol, and 4.5 g of 1-(2, 3, 4-trimethoxybenzylcarbamoyl)-5-fluorouracil (melting point: 159° C.) was obtained (Compound No. 7). NMR: 2.74 (6H s CH3) 2.98 (3H s CH3) 4.48 (2H d CH2) 6.7-7.1 (2H m C6H2) 8.42 (H d C6 -H) 9.56 (H s NH).

Workup

  1. temperaturethe solution was cooled to 5° C.
  2. temperaturethe temperature was raised to 20° C. in 2 hr
  3. customAfter removing precipitate, pyridine
  4. customwas evaporated from the solution
  5. additionHydrochloric acid water and dichloromethane were added to the remainder
  6. customthe dichloromethane layer was evaporated
  7. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-303fc5a9e89c424faa09c0845992a4cb
Source dataset
uspto-grants-1985_02
Patent number
US04497815

Reaction notes

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