Triethylamine → HCID 86745071, compound

HRID 728657Notes

Reaction equation

HRID 728657 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](CO)[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.[CH2:19](N(CC)CC)C.[NH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33].[OH-:34].[Na+]>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C:11]2([CH2:19][OH:34])[CH2:15][CH2:14][CH:13]=[CH:12]2)=[C:4]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 199606-Amino-1-hexanol2×HCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 86745071HCID 86745071, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-(cis)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol from Example 4 (0.544 g 2 mmol), triethylamine (0.607 g, 6 mmol) and 6-amino-1-hexanol (0.234 g, 2 mmol) in ethanol (5 mL) was refluxed under nitrogen for 32 hours. During this time additional 6-amino-1-hexanol (0.117 g, 1 mmol) was added. 1 N NaOH (2 mL) was then added and the solution allowed to stir for 30 minutes. The solution was concentrated under vacuum, and the residual oil was dried by evaporation of ethanol and chromatographed on silica gel. Title compound was eluted with 7% methanolchloroform; white powder after crystallization from acetonitrile (0.473 g, 68%), m.p. 120-121° C.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. dry with materialthe residual oil was dried by evaporation of ethanol
  3. customchromatographed on silica gel
  4. washTitle compound was eluted with 7% methanolchloroform
  5. customwhite powder after crystallization from acetonitrile (0.473 g, 68%), m.p. 120-121° C.

Sources & evidence

ORD record
ord-33a6741cbf8b49dab359f5866806cbcd
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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