Triethylamine → N(6)-(2-Hydroxyethyl)-N(6)-(2-methoxy-5-chlorobenzyl)-adenosine

HRID 1659090Notes

Reaction equation

HRID 1659090 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]1[OH:13].[OH:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[O:32][CH3:33].C(N(CC)CC)C>C(O)CCC>[OH:20][CH2:21][CH2:22][N:23]([CH2:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[O:32][CH3:33])[C:2]1[C:3]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=[CH:9][N:10]=1)[C@@H:11]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]1[OH:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 47233142-[(5-Chloro-2-methoxybenzyl)amino]ethanol

Product 1

HCID 22791269N(6)-(2-Hydroxyethyl)-N(6)-(2-methoxy-5-chlorobenzyl)-adenosine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5.7 g. 6-Chloro-9-(β-D-ribofuranosyl)-purine, 6 g. N-(2-hydroxyethyl)-2-methoxy-5-chlorobenzylamine and 2.5 g. triethylamine were heated under reflux for 2 hours in 100 ml. n-butanol. Subsequently, the solvent was removed in a vacuum and the residue taken up in 100 ml. chloroform. The chloroform phase was washed several times with water, initially with the addition of some dilute hydrochloric acid and thereafter with a dilute solution of sodium bicarbonate. From the so purified chloroform solution, there crystallized out 4.9 g. (53% of theory) N(6)-(2-hydroxyethyl)-N(6)-(2-methoxy-5-chlorobenzyl)-adenosine, which melted at 98°-100°C.

Workup

  1. temperatureunder reflux for 2 hours in 100 ml
  2. customSubsequently, the solvent was removed in a vacuum
  3. washThe chloroform phase was washed several times with water
  4. additioninitially with the addition of some dilute hydrochloric acid
  5. customFrom the so purified chloroform solution, there crystallized out 4.9 g

Sources & evidence

ORD record
ord-ae6f77ff805f4b2c80dc2811dbc7f95b
Source dataset
uspto-grants-1976_06
Patent number
US03966916

Reaction notes

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