Acetonitrile → HCID 492831, compound

HRID 1637735Notes

Reaction equation

HRID 1637735 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH3:11])[N:3]=1.C(#[N:20])C.[NH4+].[OH-]>O>[NH2:20][C:6]1[CH:7]=[C:2]([Cl:1])[N:3]=[C:4]([S:9][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH3:11])[N:5]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14923Ammonium HydroxideHCID 18799649HCID 18799649, compound

Product 1

HCID 492831HCID 492831, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

A flask is charged with 4,6-dichloro-2-(1-(2-pyridyl)ethyl)thio-pyrimidine (0.560 g, 1.96 mmol), acetonitrile (6.5 ml) and 13 ml of 29 % NH4OH. The contents are stirred at 35° C. for 15 h, poured into 50 ml of water, extracted once with ethyl acetate. The organic layer is washed with a saturated solution of brine (1×30 ml), dried with anhydrous Na2SO4 and concentrated in vacuo. Chromatography is accomplished with 100 g of silica gel, packed and eluted with ethyl acetate-hexane (2:3), to yield 0.491 g (94%) of 4-amino-6-chloro-2-(1-(2-pyridyl)ethyl)thio-pyrimidine.

Workup

  1. extractionextracted once with ethyl acetate
  2. washThe organic layer is washed with a saturated solution of brine (1×30 ml)
  3. dry with materialdried with anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. washeluted with ethyl acetate-hexane (2:3)

Sources & evidence

ORD record
ord-d3e0aadb222840fb802d94df5cf5f6c1
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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