Ethylamine → HCID 468297, compound

HRID 728667Notes

Reaction equation

HRID 728667 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]([NH2:21])[CH3:20].[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:21][CH2:19][CH3:20])[N:3]=1

Participants

4

Reactant 3

HCID 6341EthylamineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 468297HCID 468297, compound

Conditions

Temperature
80 °C

Procedure

(±)-cis-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.544g, 2 mmol) was added to an ethyl amine-saturated methanol solution (14 mL). The solution was heated at 80° C. in a Parr bomb for 2.5 hours. 1 N NaOH (2 mL) was added, and solvent evaporated. The residual oil was chromatographed on silica gel. Title compound was eluted with 10% methanol-chloroform; white crystals after crystallization from acetonitrile-methanol (0.365 g, 67%); mp 171-173° C.;

Workup

  1. customsolvent evaporated
  2. customThe residual oil was chromatographed on silica gel
  3. washTitle compound was eluted with 10% methanol-chloroform
  4. customwhite crystals after crystallization from acetonitrile-methanol (0.365 g, 67%)

Sources & evidence

ORD record
ord-5346ff12d8b2436ca0b96bfaf2c1f503
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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