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

HRID 728649

반응식

HRID 728649 반응식
[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]([NH2:22])[CH2:20][CH3:21].[OH-].[Na+]>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:22][CH2:19][CH2:20][CH3:21])[N:3]=1

참가 물질

5

반응물 3

HCID 7852PropylamineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

생성물 1

HCID 468298[(1S,4R)-4-[2-amino-6-(propylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of (±)-cis-4-(-2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.531 g, 2.00 mmol) from Example 4 and propylamine (1.12 g, 18.19 mmol) in 8 mL of ethanol was stirred at reflux for 2 hours. The solution was allowed to cool to room temperature before the addition of 2 mL of 1.0 N NaOH. Concentration of the solution afforded the crude product which was purified by elution from a silica gel column with 5% methanolchloroform (0.46 g, 80%). Crystallization of such a sample from ethanol-ethyl acetate yielded a white powder, m.p. 138-140° C.

후처리

  1. temperatureat reflux for 2 hours

출처 및 근거

ORD 기록
ord-c038d2137ba844208dee5d59a03f2d4e
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05049671

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