Water → HCID 90017776, compound

HRID 1055000Notes

Reaction equation

HRID 1055000 reaction equation
Br[C:2]1[C:3]([NH2:10])=[N:4][C:5]([CH3:9])=[C:6]([Cl:8])[CH:7]=1.[Li]CCCC.[CH3:16][S:17]SC.O>O1CCCC1>[Cl:8][C:6]1[CH:7]=[C:2]([S:17][CH3:16])[C:3]([NH2:10])=[N:4][C:5]=1[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 12232Dimethyl DisulfideHCID 176094393-Bromo-5-chloro-6-methylpyridin-2-amineHCID 178418339Butyllithium

Product 1

HCID 90017776HCID 90017776, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-5-chloro-6-methylpyridin-2-amine (300 mg, 1.35 mmol, Eq: 1.00) was dissolved in tetrahydrofuran (5 ml). 1.6M n-BuLi in hexanes (3.39 ml, 5.42 mmol, Eq: 4) was added at −78° C. The mixture was stirred for 10 min. 1,2-Dimethyldisulfane (510 mg, 481 μl, 5.42 mmol, Eq: 4) was added and mixture allowed to warm to room temperature. The mixture was stirred for 30 min. Water was added and the mixture was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to an oil. The product (158 mg, 61.8%) was obtained as a light yellow solid by chromatography (SiO2, ethyl acetate/n-heptane). MS: m/z=230.1 (M+acetonitrile+H+)

Workup

  1. stirringThe mixture was stirred for 30 min
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-9025c5217ce34ff78d28645e4c258211
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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