Ethanolamine → 2-(4-(3-Azidopropylamino)-6-chloro-1,3,5-triazin-2-ylamino)ethanol

HRID 1404416Notes

Reaction equation

HRID 1404416 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16](Cl)[N:15]=[C:14]([Cl:19])[N:13]=1)=[N+:6]=[N-:7]>CC(C)=O>[N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:13]=[C:14]([Cl:19])[N:15]=[C:16]([NH:4][CH2:3][CH2:1][OH:2])[N:17]=1)=[N+:6]=[N-:7]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 86672179N-(3-azidopropyl)-4,6-dichloro-1,3,5-triazin-2-amine

Product 1

HCID 866721782-(4-(3-Azidopropylamino)-6-chloro-1,3,5-triazin-2-ylamino)ethanolYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Ethanolamine (2.47 g, 40.4 mmol) in acetone (20 mL) was added to a solution of 1 (2.0 g, 8.1 mmol) in acetone (30 mL). The reaction was stirred at room temperature for 24 hours. The acetone was removed by rotary evaporation and the residue was suspended in CH2Cl2. The mixture was filtered off. The solid collected was washed with CH2Cl2 with H2O and dried under reduced pressure to afford 2 as a white solid (1.86 g, 85%). The product is sufficiently pure for further reactions. ESI-MS m/z 273.1 (M+H+) calculated for C8H14ClN8O 273.1.

Workup

  1. customThe acetone was removed by rotary evaporation
  2. filtrationThe mixture was filtered off
  3. customThe solid collected
  4. washwas washed with CH2Cl2 with H2O
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-e46ae5180b6c47dca94b788e95b4ccbc
Source dataset
uspto-grants-2014_12
Patent number
US08912323B2

Reaction notes

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