Methylamine → [(1S,4R)-4-[2-amino-6-(methylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol

HRID 728650Notes

Reaction equation

HRID 728650 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.[CH3:19][NH2:20].[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:20][CH3:19])[N:3]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 468296[(1S,4R)-4-[2-amino-6-(methylamino)purin-9-yl]cyclopent-2-en-1-yl]methanolYield 70%

Procedure

(±)-cis-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.400 g, 1.5 mmol) from Example 4 and methylamine (40% aqueous solution, 25 mL) were stirred at 60° C. for 0.5 hours. The solution was allowed to cool to room temperature before the addition of 1.5 mL of 1.5 N NaOH. Evaporation left the crude product which was purified by elution from a silica gel column with 5% methanolchloroform. The resulting solid was slurried in acetonitrile to yield a pale yellow powder (0.274 g, 70%); m.p. 221-223° C.

Workup

  1. customEvaporation
  2. waitleft the crude product which
  3. customwas purified by elution from a silica gel column with 5% methanolchloroform

Sources & evidence

ORD record
ord-646f4a9e4ab648e48ecc3903d32c9db1
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

Loading…