Isopropyl iodide → Isopropyl purine

HRID 361879Notes

Reaction equation

HRID 361879 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2C(C)C)=[C:4](NCC2C=CC(OC)=CC=2)[N:3]=1.CO[C:26]1[CH:43]=CC(CNC2N=C(Cl)N=C3C=2NC=N3)=C[CH:27]=1.[H-].[Na+].IC(C)C>CN(C=O)C.O>[CH:26]([C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[CH:4][N:3]=1)([CH3:43])[CH3:27]

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 98587852-Chloro-9-isopropyl-N-(4-methoxybenzyl)-9H-purin-6-amineHCID 164220562-Chloro-N-(4-methoxybenzyl)-9H-purin-6-amine

Product 1

HCID 18473604Isopropyl purineYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Preparation of 2-chloro-6-(4-methoxybenzylamino)-9-isopropylpurine (2) The 6-(4-methoxybenzylamino)-2-chloropurine (496 mg, 1.7 mmol) was suspended in dry DMF (5 ml) and treated with sodium hydride, 60% dispersion (82 mg, 2.06 mmol). The suspension was stirred for 30 min over which time it became a clear yellow/green solution. 2-Iodopropane (0.280 mL, 1.7 eq.) was added over 5 min and the resultant solution stirred for 2 days. Water was added and the solution and extracted with ethyl acetate. The organic layer was evaporated to give the product isopropyl purine (508 mg, 89%).

Workup

  1. extractionthe solution and extracted with ethyl acetate
  2. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-04655bddf1e441ed9ea634d9d34ca14a
Source dataset
uspto-grants-1999_02
Patent number
US05866702

Reaction notes

Loading…