Cadaverine → N-(5-aminopentyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2281447Notes

Reaction equation

HRID 2281447 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18].C(N(CC)CC)C>C(O)CCC>[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:4]1[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1

Participants

5

Reactant 3

HCID 273CadaverineHCID 8471TriethylamineHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86636620N-(5-aminopentyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 84.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (70 mg, 0.37 mmol), 1,5-diaminopentane (0.130 mL, 1.11 mmol) and triethylamine (0.150 mL, 1.08 mmol) in nBuOH (3 mL) was stirred at 70° C. for 1 h. It was then purified by HPLC to give N-(5-aminopentyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine as a solid (79 mg).

Workup

  1. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-a2c3866fbc004f3aac74b9814c87f2cd
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

Loading…