Sodium cyanoborohydride → [9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-ylmethyl]-cyclohexylamine

HRID 1246819Notes

Reaction equation

HRID 1246819 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][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[CH2:25]N)=[CH:4][CH:3]=1.[C:27]([BH3-])#[N:28].[Na+]>CO.C1(=O)CCCCC1.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[CH2:25][NH:28][CH:27]2[CH2:6][CH2:7][CH2:2][CH2:3][CH2:4]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 21905813C-[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-yl]-methylamine

Product 1

HCID 21905835[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-ylmethyl]-cyclohexylamine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 7967CyclohexanoneCatalystHCID 887MethanolSolvent

Procedure

C-[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-yl]-methylamine I-(16A-1)b (19 mg, 0.047 mmol) was dissolved in methanol (1 ml) and to it was added cyclohexanone (1 drop) and acetic acid (1 drop). The reaction mixture was stirred at room temperature for 0.5 hour. and then sodium cyanoborohydride was added (5 mg) and the stirring continued until the reaction was complete (2 hours). The reaction mixture was concentrated and the residue diluted with saturated NaHCO3 solution and extracted into ethyl acetate. The organic layers were combined, dried (Na2SO4), filtered, and 5% methanol in ethyl acetate as the solvent to give title compound 16A-1. The residue was dissolved in methylene chloride and treated with 2M HCl/ether to form the desired HCl salt. Ether was added to the reaction mixture to precipitate the product. The excess ether was decanted and the crystals pumped to dryness on high vacuum to afford the hydrochloride salt of compound 16A-1 (6.8 mg, 30%): +ESI MS (M+1) 486.6; 1H NMR (500 MHz, CD3OD) δ 9.07 (s, 1H), 7.71 (d, J=8.8 Hz, 1H), 7.64 (d, J=2.1 Hz, 1H), 7.56 (dd, J=8.8, 2.1 Hz, 1H), 7.52 (d, J=8.8 Hz, 2H), 7.40 (d, J=8.8 Hz, 2H), 4.94 (s, 2H), 3.35 (m 1H), 2.28 (br d, J=12.4 Hz, 2H), 1.96 (br d, J=13.5 Hz, 2H), 1.78 (br d, J=13.0 Hz, 1H), 1.60–1.20 (m, 5H).

Workup

  1. custom(2 hours)
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue diluted with saturated NaHCO3 solution
  4. extractionextracted into ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-65ec8e16bc8243f6be09b983dfd2e266
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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