Acetic Acid → HCID 21265576, compound

HRID 566186Notes

Reaction equation

HRID 566186 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[C:5]([N+:14]([O-])=O)=[CH:4][C:3]=1[N:17]1[C:22](=[O:23])[C:21]([CH3:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[N:19]([CH3:29])[C:18]1=[O:30].C(O)(=O)C.O>[Fe].C(O)C>[NH2:14][C:5]1[C:6]([C:8]#[C:9][Si:10]([CH3:13])([CH3:11])[CH3:12])=[CH:7][C:2]([F:1])=[C:3]([N:17]2[C:22](=[O:23])[C:21]([CH3:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[N:19]([CH3:29])[C:18]2=[O:30])[CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 21265575HCID 21265575, compound

Product 1

HCID 21265576HCID 21265576, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture consisting of 3-{2-fluoro-5-nitro-4-[2-(trimethylsilyl)-1-ethynyl]phenyl}-1,5-dimethyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (11.95 g), iron powder (15.68 g), acetic acid (14 ml), water (14 ml) and ethanol (280 ml) was heated to 80° C. and stirred for 3 hours. Then, the solvent was distilled off under reduced pressure. An aqueous sodium hydroxide solution was added thereto to make it alkaline. Then, methylene chloride was added thereto for extraction. After washing with water, it was dried over anhydrous magnesium sulfate. Then, methylene chloride was distilled off, and the resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:3 v/v) to obtain 3-{5-amino-2-fluoro-4-[2-(trimethylsilyl)-1-ethynyl]-phenyl}-1,5-dimethyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (7.70 g).

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. additionAn aqueous sodium hydroxide solution was added
  3. additionThen, methylene chloride was added
  4. extractionfor extraction
  5. washAfter washing with water, it
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. distillationThen, methylene chloride was distilled off
  8. customthe resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:3 v/v)

Sources & evidence

ORD record
ord-e5c1a4cf220743e8979bbd93b914a364
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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