Hexachloroethane → HCID 178429499, compound

HRID 630161Notes

Reaction equation

HRID 630161 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[CH:13]=[N:12][CH:11]=2)[N:5]=[C:4]([OH:18])[CH:3]=1.[Li]CCCC.[Cl:24]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.CO>[Cl:24][C:13]1[N:14]([CH:15]([CH3:16])[CH3:17])[C:10]([CH2:9][S:8][C:6]2[N:5]=[C:4]([OH:18])[CH:3]=[C:2]([CH3:1])[N:7]=2)=[CH:11][N:12]=1

Participants

6

Reactant 3

HCID 6214HexachloroethaneHCID 178418339ButyllithiumHCID 178429507HCID 178429507, compound

Product 1

HCID 178429499HCID 178429499, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 mL round bottom flask, 6-methyl-2-({[1-(propan-2-yl)-1H-imidazol-5-yl]methyl}sulfanyl)pyrimidin-4-ol (260 mg, 1.0 mmol) was dissolved in THF (20 mL) at −78° C. BuLi (0.88 mL, 2.2 mmol) was added dropwise. After 1 hour, hexachloroethane (360 mg, 1.5 mmol) was added. The resulting mixture was stirred at 0° C. for 2 hours. A few drops of methanol were added to quench the reaction. Then, the solvent as removed under vacuum, and the crude was purified by column chromatography to provide the title compound as a white solid (200 mg, 87% yield); 1H NMR (400 MHz, CD3OD): δ 1.45 (d, 6H), 2.20 (s, 3H), 4.46 (s, 2H), 4.62 (m, 1H), 6.02 (bs, 1H), 6.84 (s, 1H); M+299.

Workup

  1. customto quench
  2. customthe reaction
  3. customThen, the solvent as removed under vacuum
  4. customthe crude was purified by column chromatography

Sources & evidence

ORD record
ord-30bde9fa2f8b4954b3393a2a85121677
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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