Water → 2-[4-chloro-2-fluoro-5-(3-bromo-2-propynyloxy)phenyl]-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione

HRID 35427Notes

Reaction equation

HRID 35427 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([O:10][CH2:11][C:12]#[CH:13])=[CH:8][C:7]([N:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[CH:16]=[N:15]2)=[C:6]([F:23])[CH:5]=1.[Br:24]Br.O>O1CCCC1>[Cl:3][C:4]1[C:9]([O:10][CH2:11][C:12]#[C:13][Br:24])=[CH:8][C:7]([N:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[CH:16]=[N:15]2)=[C:6]([F:23])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 24758Sodium hydrideHCID 142769522-(4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4-methyl-1,2,4-triazine-3.5(2H,4H)-dione2×

Product 1

HCID 142769682-[4-chloro-2-fluoro-5-(3-bromo-2-propynyloxy)phenyl]-4-methyl-1,2,4-triazine-3,5(2H,4H)-dioneYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred mixture of 0.05 g (0.002 mole) of sodium hydride in 5 mL of tetrahydrofuran was added a solution of 0.55 g (0.0018 mole) of 2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione (Compound 21, see Example III, Step J) in 5 mL of tetrahydrofuran. To this mixture was added a solution of 0.28 g (0.0018 mole) of bromine in 5 mL of tetrahydrofuran. After complete addition, the reaction mixture was stirred at room temperature for one hour. Water, 5 mL, was added to the mixture, and the total stirred at room temperature for two days. The mixture was partitioned between water and ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 0.45 g of 2-[4-chloro-2-fluoro-5-(3-bromo-2-propynyloxy)phenyl]-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione as a solid (mp 127°-129° C.), Compound 48 in the tables.

Workup

  1. additionAfter complete addition
  2. stirringthe total stirred at room temperature for two days
  3. customThe mixture was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a41d4c9c39d243c79d1d10ad14e62cfd
Source dataset
uspto-grants-1988_08
Patent number
US04766233

Reaction notes

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