Isopropyl iodide → HCID 89442470, compound

HRID 2284019Notes

Reaction equation

HRID 2284019 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[CH:17]([CH3:19])[CH3:18]>CC(C)=O>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH2:1])[C:7]=1[O:8][CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 130128854-Amino-6-chloropyrimidin-5-ol

Product 1

HCID 89442470HCID 89442470, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

A reaction mixture of 4-Amino-6-chloro-pyrimidin-5-ol (500.00 mg; 3.44 mmol; 1.00 eq.), Cs2CO3 (2238.59 mg; 6.87 mmol; 2.00 eq.), and 2-Iodo-propane (1167.95 mg; 6.87 mmol; 2.00 eq.) in acetone 10 ml was stirred at 65° C. for 3 hr, desired as major, also found dialkylation by product, removed off solvent, treated with ethyl acetate, solid came out, filtered, washed with ether, collected product 6-chloro-5-isopropoxypyrimidin-4-amine 160 mg, yield 24.8%

Workup

  1. customremoved off solvent
  2. additiontreated with ethyl acetate, solid
  3. filtrationfiltered
  4. washwashed with ether

Sources & evidence

ORD record
ord-875ca0d6b63a495db17d78e58312dfe7
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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