Isopropyl iodide → 9-(4-Chlorophenyl)-8-(2-chlorophenyl)-6-isopropoxy-9H-purine

HRID 1246828Notes

Reaction equation

HRID 1246828 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[OH:24])=[CH:4][CH:3]=1.I[CH:26]([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[O:24][CH:26]([CH3:28])[CH3:27])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodide2×HCID 10796Cesium carbonate2×HCID 178517925HCID 178517925, compound

Product 1

HCID 219058479-(4-Chlorophenyl)-8-(2-chlorophenyl)-6-isopropoxy-9H-purine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

9-(4-Chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-ol (I-(4A-7)b; 50 mg, 0.14 mmol), 2-iodopropane (26 mg, 0.15 mmol), and cesium carbonate (50 mg, 0.15 mmol) were combined in dimethylformamide (0.7 ml) and stirred overnight. Additional 2-iodopropane (13 mg, 0.76 mmol), and cesium carbonate (25 mg, 0.76 mmol) were added and stirred an addional day. The reaction mixture was diluted with ethyl ether and then washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried (Na2SO4), evaporated to dryness, and then purified on a Biotage™ Flash 12S column using 0–70% ethyl acetate in hexanes as eluant to afford title compound 31A-1 (34 mg, 56%); 1H NMR: +ESI MS (M+1) 399.4; (400 MHz, CD2Cl2) δ 8.51 (s, 1H), 7.56 (dd, J=7.5, 1.7 Hz, 1H), 7.47–7.34 (m, 5H), 7.23 (d, J=9.1 Hz, 2H), 5.71 (septuplet, J=6.2 Hz, 1H), 1.50 (d, J=6.2 Hz, 6H).

Workup

  1. stirringstirred an addional day
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated to dryness
  5. custompurified on a Biotage™ Flash 12S column

Sources & evidence

ORD record
ord-cc55c678722e46bfa340841c3b0cca91
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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