Iodoethane → HCID 57899156, compound

HRID 1036332Notes

Reaction equation

HRID 1036332 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-e4864f3ec9d34b49b522d29623047e55
Source dataset
uspto-grants-2013_10
Patent number
US08546407B2

Reaction notes

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