1-Butanol → HCID 12783669, compound

HRID 1679352Notes

Reaction equation

HRID 1679352 reaction equation
[Na].Cl[C:3]1[NH:8][C:7](=[O:9])[C:6]([F:10])=[CH:5][N:4]=1.[CH2:11]([OH:15])[CH2:12][CH2:13][CH3:14]>>[CH2:11]([O:15][C:3]1[NH:8][C:7](=[O:9])[C:6]([F:10])=[CH:5][N:4]=1)[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 2553942-Chloro-5-fluoropyrimidin-4(3H)-oneHCID 5360545Sodium

Product 1

HCID 12783669HCID 12783669, compoundYield 91.9%

Procedure

A 5.8 g quantity of metal sodium is dissolved in 300 ml of absolute n-butanol, 14.9 g of 2-chloro-5-fluoropyrimidin-4-one is added to the solution and the mixture is heated in a sealed tube at 140° to 150° C for 5 hours for reaction. The solvent is distilled off from the reaction mixture, 50 ml of water is added to the residue and the pH of the mixture is adjusted to 4-5 to separate out crystals, which are recrystallized from ethanol to give 17.1 g of white crystalline 2-n-butoxy-5-fluoropyrimidin-4-one in a yield of 91.9 %, m.p. 127°-129° C.

Workup

  1. temperaturethe mixture is heated in a sealed tube at 140° to 150° C for 5 hours for reaction
  2. distillationThe solvent is distilled off from the reaction mixture, 50 ml of water
  3. additionis added to the residue
  4. customto separate out crystals, which
  5. customare recrystallized from ethanol

Sources & evidence

ORD record
ord-8c27ee847a31455a85af54c37725b4c1
Source dataset
uspto-grants-1978_03
Patent number
US04080455

Reaction notes

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