2-(4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4-methyl-1,2,4-triazine-3.5(2H,4H)-dione → HCID 19863061, compound

HRID 1164731Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N:12]2[C:17](=[O:18])[N:16]([CH3:19])[C:15](=[O:20])[CH:14]=[N:13]2)=[C:4]([F:21])[CH:3]=1>C(O)(=O)C.O.[Zn]>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N:12]2[C:17](=[O:18])[N:16]([CH3:19])[C:15](=[O:20])[CH2:14][NH:13]2)=[C:4]([F:21])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 1.6 g (0.0052 mole) of 2-(4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4-methyl-1,2,4-triazine-3.5(2H,4H)-dione (compound 21) dissolved in 5 mL of glacial acetic acid was added dropwise to a stirred suspension of 1.5 g (0.023 mole) of zinc dust in 10 mL of glacial acetic acid and 5 mL of water. After complete addition the mixture was heated at 60° C. for 1.5 hours. The mixture was filtered and the filtrate was partitioned between 50 mL of water and 50 mL of diethyl ether. The organic phase was washed first with water followed by a saturated aqueous sodium bicarbonate solution. The washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 1.2 g of 2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-1,6-dihydro-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione as an oil, compound A-3 of Table A-1.

Workup

additionAfter complete addition the mixture
filtrationThe mixture was filtered
customthe filtrate was partitioned between 50 mL of water and 50 mL of diethyl ether
washThe organic phase was washed first with water
dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
filtrationfiltered
customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-197c743dfdce4b2bbd4438a1ac0cbc3f
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04906287

Reaction notes

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