Hydrochloric Acid → 1-[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-yl]-ethanone

HRID 1246799Notes

Reaction equation

HRID 1246799 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.C([Sn](CCCC)(CCCC)[C:31]([O:33]CC)=[CH2:32])CCC.O.Cl>CN(C)C=O.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:6]2[C:5]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[C:31](=[O:33])[CH3:32])=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 219058016-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine

Product 1

HCID 219057891-[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-yl]-ethanone

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 6-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine I-(1A-1)d (202 mg, 0.49 mmol) and tetrakis(triphenylphosphine) palladium(0) (60 mg, 0.049 mmol) in dimethylformamide (1.5 ml) was degassed and to it was added tributyl-(1-ethoxyvinyl)-stannane (250 μl, 0.74 mmol). The reaction mixture was heated to 100° C. until completed as shown by TLC. A solution of 2:1 of H2O/conc. HCl (1.5 ml) was added to the reaction mixture and the heating continued for 1 hour. The reaction was diluted with ethyl acetate and washed with water. The organic layers were combined, dried (Na2SO4), filtered, and concentrated to dryness. The crude material was purified via TLC preparative plate using 30% ethyl acetate/hexanes as the solvent to afford the desired product I-(15A-1)a (50 mg, 25%): +ESI MS (M+1) 417.3; 1H NMR (400 MHz, CDCl3) δ 9.11 (s, 1H), 7.58 9 (d, J=8.7 Hz, 1H), 7.43–7.30 (m, 4H), 7.21 (d, J=8.7 Hz, 2H), 2.92 (s, 3H).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude material was purified via TLC preparative plate

Sources & evidence

ORD record
ord-d9271f3365d346a0afe698e59a8babe9
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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