6-Bromo-1,2,4-triazin-3-amine → HCID 67454331, compound

HRID 2276781Notes

Reaction equation

HRID 2276781 reaction equation
Br[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[N:4][CH:3]=1.[Br-].[Si:10]([O:17][CH2:18][C:19]1[S:23][C:22]([Zn+])=[N:21][CH:20]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[Si:10]([O:17][CH2:18][C:19]1[S:23][C:22]([C:2]2[N:7]=[N:6][C:5]([NH2:8])=[N:4][CH:3]=2)=[N:21][CH:20]=1)([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:11])[CH3:12]

Participants

5

Reactant 2

HCID 153325646-Bromo-1,2,4-triazin-3-amineHCID 178455169HCID 178455169, compound

Product 1

HCID 67454331HCID 67454331, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

In a separate flask was added 6-bromo-1,2,4-triazin-3-amine (10.0 g, 57.5 mmol), (PPh3)4Pd (12.1 g, 11.5 mmol), and THF (200 mL). The mixture was heated to 80° C., followed by the dropwise addition (1 h) of (5-((tert-butyldimethylsilyloxy)methyl)thiazol-2-yl)zinc(II) bromide prepared in the step above. The reaction was then cooled to rt, filtered through a silica pad, concentrated, and then purified using silica gel chromatography to afford 6.7 g the title compound as a light yellow solid.

Workup

  1. customprepared in the step above
  2. temperatureThe reaction was then cooled to rt
  3. filtrationfiltered through a silica pad
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-087565f61f544a1080e7a6b73912d96d
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

Loading…