Potassium Carbonate → 9-Butyl-8-(2-iodo-5-methoxy-benzyl)-9H-purin-6-ylamine

HRID 1295470Notes

Reaction equation

HRID 1295470 reaction equation
[CH2:1]([N:5]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:23])[CH2:2][CH2:3][CH3:4].[I:24]NC(=O)CCC(N)=O.C([O-])([O-])=O.[K+].[K+]>CC(O)=O.C(Cl)Cl>[CH2:1]([N:5]1[C:13]([CH2:14][C:15]2[CH:16]=[C:17]([O:21][CH3:22])[CH:18]=[CH:19][C:20]=2[I:24])=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:23])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 52892289-Butyl-8-(3-Methoxybenzyl)-9h-Purin-6-AmineHCID 21864724N-Iodosuccinamide2×

Product 1

HCID 116764699-Butyl-8-(2-iodo-5-methoxy-benzyl)-9H-purin-6-ylamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

4.1 To a solution of 9-butyl-8-(3-methoxy-benzyl)-9H-purin-6-ylamine (1.24 g, 4 mmol) in AcOH (6 ml) was added N-iodo-succinamide (NIS) (1.8 g, 8 mmol). After 3 h at r.t., additional NIS (1.8 g, 8 mmol) was added, and the mixture was stirred for another 24 h. The reaction mixture was diluted with CH2Cl2 (500 ml), and carefully neutralized with a solution of sat. aq. K2CO3 (2×100 ml), then washed with 0.1 N Na2S2O3 (3×100 ml), brine (3×100 ml), dried (Na2SO4), evaporated, and purified by flash chromatography (CH2Cl2:MeOH=100:5) to give the 9-Butyl-8-(2-iodo-5-methoxy-benzyl)-9H-purin-6-ylamine (4.1), as a colorless powder (0.53 g, 30%); rt=7.7 min.; 1HNMR (CDCl3-d) δ 8.36 (s, 1H), 7.77 (d, J=7.9 Hz, 1H), 6.68 (s, 1H), 6.61 (d, J=7.9 Hz, 1H), 5.62 (s, 2H), 4.33 (s, 2H), 4.06 (t, J=7.7 Hz, 2H), 3.72 (s, 3H), 1.67 (quint., J=7.7 Hz, 2H), 1.36 (sext., J=7.5 Hz, 2H), 0.92 (t, J=7.4 Hz, 3H).

Workup

  1. washwashed with 0.1 N Na2S2O3 (3×100 ml), brine (3×100 ml)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. custompurified by flash chromatography (CH2Cl2:MeOH=100:5)

Sources & evidence

ORD record
ord-7e82f4bab7aa4a4d9ddb2b89b3f48c48
Source dataset
uspto-grants-2007_07
Patent number
US07241890B2

Reaction notes

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