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

HRID 728651

Reaction equation

HRID 728651 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.[OH-].[Na+].[CH3:21][NH:22][CH3:23]>>[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]([N:22]([CH3:23])[CH3:21])[N:3]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 468299[(1S,4R)-4-[2-amino-6-(dimethylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol

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 dimethylamine (25% aqueous solution, 20 mL) was stirred at 80° C. for 0.5 hours. The reaction mixture was allowed to cool to room temperature before the addition of 1.5 mL of 1 N NaOH. Concentration of the solution afforded the crude product which was purified by elution from a silica gel column with 5% methanol-chloroform (0.310 g, 75%). Crystallization of such a sample from ethanol-water gave an off-white powder m.p. 173-174° C.:

Workup

  1. customConcentration of the solution afforded the crude product which
  2. customwas purified by elution from a silica gel column with 5% methanol-chloroform (0.310 g, 75%)
  3. customCrystallization of such a sample from ethanol-water

Sources & evidence

ORD record
ord-3a6fb1b298f342bab08401845f9e5c2d
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Linked notes

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