Morpholine → (+/-)-cis-4-(2-Amino-6-morpholino-9H-purin-9-yl)-2-cyclopentene-1-methanol

HRID 728648

반응식

HRID 728648 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.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[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]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

생성물 1

HCID 67795685(+/-)-cis-4-(2-Amino-6-morpholino-9H-purin-9-yl)-2-cyclopentene-1-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 morpholine (0.526 g, 6.04 mmol) in ethanol (6 mL) was stirred at reflux for 1 hour. The reaction mixture was allowed to cool to room temperature before the addition of 2 mL of 1.0 N NaOH. Concentration of the mixture afforded the crude product which was purified by elution from a silica gel column using 5% methanol in chloroform (0.62 g, 98%). Crystallization of such a sample from ethanol-water gave a white powder; m.p. 165-167° C.

후처리

  1. temperatureat reflux for 1 hour

출처 및 근거

ORD 기록
ord-a582c7518406493b858274d68fa554dc
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05049671

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