Sodium Hydroxide → HCID 86745070, compound

HRID 728654Notes

Reaction equation

HRID 728654 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.[CH2:19]1[CH:23]([CH2:24][OH:25])[CH2:22][CH:21]([NH2:26])[CH2:20]1.[OH-].[Na+]>C(N(CC)CC)C.C(O)C>[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:26][C@H:21]2[CH2:20][CH2:19][C@@H:23]([CH2:24][OH:25])[CH2:22]2)[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-HCID 14016457HCID 14016457, compound

Product 1

HCID 86745070HCID 86745070, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent2×

Procedure

A solution of (±)-cis-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (530 mg, 2.00 mmol) from Example 4, 3-aminocyclopentyl-1-methanol (276 mg, 24 mmol), triethylamine (1.12 g, 10.98 mmol), and ethanol (20 mL) was stirred at reflux for 5 hours. An additional amount of triethylamine (1.17 g) was then added and the solution was refluxed for 8 additional hours. The solution was allowed to cool to room temperature and 2 mL of 1 N NaOH was added. The solution was concentrated and the residues were placed on silica gel column which was eluted with 10% methanol-chloroform (0.36 g, 52%). Recrystallization of such a sample from ethanolacetonitrile gave title compound as white powder, m.p. 177-180° C.

Workup

  1. temperatureat reflux for 5 hours
  2. temperaturethe solution was refluxed for 8 additional hours
  3. concentrationThe solution was concentrated
  4. washwas eluted with 10% methanol-chloroform (0.36 g, 52%)
  5. customRecrystallization of such a sample

Sources & evidence

ORD record
ord-ca81487c6ec64034a693aa86d030f438
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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