HCID 13061617, compound → HCID 13061618, compound

HRID 1679350Notes

Reaction equation

HRID 1679350 reaction equation
[CH2:1]([O:17][C:18]1[N:23]=[C:22]([O:24]CCCCCCCCCCCCCCCC)[C:21]([F:41])=[CH:20][N:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>[OH-].[K+].C(O)C>[CH2:1]([O:17][C:18]1[NH:23][C:22](=[O:24])[C:21]([F:41])=[CH:20][N:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 1

HCID 13061617HCID 13061617, compound

Product 1

HCID 13061618HCID 13061618, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A 2.9 g portion of the 2,4-di-(n-hexadecyloxy)-5-fluoropyrimidine is dissolved in a mixture of 5 ml of 2N aqueous potassium hydroxide solution and 25 ml of ethanol, and the solution is refluxed for 4 hours. The ethanol is distilled off from the resulting reaction mixture, and 50 ml of ether is added to the residue to remove ether-soluble substances. Dilute hydrochloric acid is added to the remaining mass to adjust the pH to 4-5 and to separate out crystals, which are recrystallized from ethanol to give 1.3 g of white crystalline 2-n-hexadecyloxy-5-fluoropyrimidin-4-one in a yield of 73.0 %, m.p. 97°-98° C.

Workup

  1. temperaturethe solution is refluxed for 4 hours
  2. distillationThe ethanol is distilled off from the resulting reaction mixture, and 50 ml of ether
  3. additionis added to the residue
  4. customto remove ether-soluble substances
  5. additionDilute hydrochloric acid is added to the remaining mass
  6. customto separate out crystals, which
  7. customare recrystallized from ethanol

Sources & evidence

ORD record
ord-db74375bef964095bb753fe87f99474b
Source dataset
uspto-grants-1978_03
Patent number
US04080455

Reaction notes

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