Ethanolamine → HCID 67796390, compound

HRID 728653Notes

Reaction equation

HRID 728653 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[CH2:26]([CH2:28][NH2:29])[OH:27].COC(O)C.[OH-].[Na+]>>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4]([NH:29][CH2:28][CH2:26][OH:27])[N:3]=1

Participants

6

Reactant 5

HCID 700EthanolamineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-HCID 30156371-Methoxyethanol

Product 1

HCID 67796390HCID 67796390, compound

Procedure

A flask charged with (±)-cis-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.53 g, 2.00 mmol) from Example 4, triethylamine (0.92 g, 9.10 mmol), ethanolamine (0.172 g, 2.82 mmol) and methoxyethanol (6 mL) was stirred at reflux for 2 hours. The solution was allowed to cool to room temperature before the addition of 2 mL of 1.0 N NaOH. Concentration of the solution left the crude product which was purified by elution from a silica gel column with 10% methanol chloroform (0.430 g, 74%). Crystallization of such a sample from ethanol-water gave a white powder, m.p. 150-152° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customwas purified by elution from a silica gel column with 10% methanol chloroform (0.430 g, 74%)
  3. customCrystallization of such a sample from ethanol-water
  4. customgave a white powder, m.p. 150-152° C.

Sources & evidence

ORD record
ord-49d3c6236af54e788fc7c40afcf73cd6
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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