Iodoethane → HCID 57899156, compound

HRID 2405986Notes

Reaction equation

HRID 2405986 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([NH2:10])=[C:8]([Cl:11])[N:7]=[CH:6][N:5]=1.[CH2:12](I)[CH3:13]>CN(C=O)C.[Cl-].[NH4+].O>[CH2:12]([NH:10][C:9]1[C:4]([Cl:3])=[N:5][CH:6]=[N:7][C:8]=1[Cl:11])[CH3:13]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 57899156HCID 57899156, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Sodium hydride (55%, 0.17 g, 4.0 mmol) was added in a single portion to a solution of (4,6-dichloropyrimidin-5-yl)amine (0.61 g, 3.72 mmol) and ethyl iodide (0.30 mL, 3.8 mmol) in dry DMF (3 mL) at room temperature. The suspension was stirred for 18 hours, then diluted with saturated aqueous ammonium chloride (5 mL) and water (20 mL). The mixture was extracted with diethyl ether (30 mL), and the extract was dried, filtered and concentrated. Flash column chromatography on silica, eluting with 10% ethyl actetate-hexanes, gave ethyl(4,6-dichloropyrimidin-5-yl)amine (0.321 g, 1.67 mmol, 45%). LC-MS (LCT2) m/z 192, 194 [M+H+], Rt 6.07 min.

Workup

  1. extractionThe mixture was extracted with diethyl ether (30 mL)
  2. customthe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washFlash column chromatography on silica, eluting with 10% ethyl actetate-hexanes

Sources & evidence

ORD record
ord-be859af0b3df4a41b7b4d02c30f7f0fe
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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