Iodoethane → 6-Chloro-5-ethoxypyrimidin-4-amine

HRID 2283938Notes

Reaction equation

HRID 2283938 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:17][CH3:18]>CC(C)=O.C(OCC)(=O)C>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH2:1])[C:7]=1[O:8][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 130128854-Amino-6-chloropyrimidin-5-ol

Product 1

HCID 735550476-Chloro-5-ethoxypyrimidin-4-amineYield 98.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A reaction mixture of 4-amino-6-chloro-pyrimidin-5-ol (1000.0 mg; 6.8 mmol; 1.0 eq.), cesium carbonate (2686.3 mg; 8.24 mmol; 1.2 eq.), and iodoethane (1285.9 mg; 8.24 mmol; 1.2 eq.) in acetone (10 ml) was stirred at 50° C. overnight. The reaction solution was diluted with ethyl acetate (50 ml), washed with water, then brine, dried and concentrated. The residue was treated with ether, stirred for 30 min, filtered, collected white off solid as title compound (1165 mg in yield 98%).

Workup

  1. washwashed with water
  2. dry with materialbrine, dried
  3. concentrationconcentrated
  4. additionThe residue was treated with ether
  5. stirringstirred for 30 min
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c9fb17d6403d41a29c4ff3efdc942cea
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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