Iodoethane → HCID 118483166, compound

HRID 1773339Notes

Reaction equation

HRID 1773339 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:17][CH3:18]>CN(C=O)C.CC(=O)OCC>[Cl:1][C:2]1[N:7]([CH2:17][CH3:18])[C:6](=[O:8])[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178516194HCID 178516194, compound

Product 1

HCID 118483166HCID 118483166, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,6-dichloro-pyrimidin-4-ol (1.0 g, 6.1 mmol) and K2CO3 (1.1 g, 7.9 mmol) in DMF (10 mL) was stirred at RT for 15 min. The reaction mixture was cooled to 0° C., and iodoethane (1.1 mL, 6.7 mmol) was added dropwise. After stirring overnight at RT, the reaction mixture was diluted with EA, washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica chromatography (20:1, EA:PE) to give 330 mg (28%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 1.37 (t, J=7.6 Hz, 3H), 4.76 (q, J=6.8 Hz, 2H), 6.67 (s, 1H). [M+H] Calc'd for C6H6Cl2N2O, 193, 195, 197. Found, 193, 195, 197.

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica chromatography (20:1, EA:PE)

Sources & evidence

ORD record
ord-de8904a5b59a4d8983cfcab81b9db49a
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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