Triethylamine → 2-chloro-N-(3-iodobenzyl)-7H-purin-6-amine

HRID 965196Notes

Reaction equation

HRID 965196 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.Cl.[I:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][NH2:18].C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:18][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([I:13])[CH:15]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27238613-Iodobenzylamine hydrochlorideHCID 53244122,6-Dichloropurine

Product 1

HCID 103179492-chloro-N-(3-iodobenzyl)-7H-purin-6-amineYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,6-dichloropurine (Aldrich Chemical Co., 1 g, 5.3 mmol), 3-iodobenzylamine hydrochloride (1.7 g, 5.8 mmol), and triethylamine (2.2 ml, 15.35 mmol) in ethanol (10 ml) was stirred for 5 days at room temperature. The colorless solid formed was collected by suction, washed with small amount of cold ethanol, and dried to yield 2-chloro-N6 -(3-iodobenzyl)adenine (1.16 g, 60%): m.p. 222°-224° C.; mass (EI) 385: 1H NMR (DMSO-d6 d 4.59 (br s, 2H, --CH2), 7.13 (pseudo t, J=8.2 and 7.5 Hz, 1H, Bn), 7.36 (d, J=7.5 Hz, 1H, Bn), 7.61 (d, J=7.5 Hz, 1H, Bn), 7.74 (s, 1H, Bn), 8.14 (s, 1H, H-8), 8.76 (br s, 1H, exchangeable with D2O, NH), 13.14 (br s, 1H, exchangeable with D2O, NH). UV (MeOH) 1max 281.7, 257.5, 232.5 nm.

Workup

  1. customThe colorless solid formed
  2. customwas collected by suction
  3. washwashed with small amount of cold ethanol
  4. customdried

Sources & evidence

ORD record
ord-a5c0adb6a8bc4171a673c244737923b7
Source dataset
uspto-grants-1998_06
Patent number
US05773423

Reaction notes

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