Purine → 4-(2-chloro-9H-purin-6-yl)morpholine

HRID 1434508Notes

Reaction equation

N1C=C2C(N=CN2)=NC=1.[Cl:10][C:11]1[N:19]=[C:18]2[C:14]([NH:15][CH:16]=[N:17]2)=[C:13](Cl)[N:12]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[Cl:10][C:11]1[N:19]=[C:18]2[C:14]([NH:15][CH:16]=[N:17]2)=[C:13]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:12]=1

Participants

Reactant 3

HCID 1044Purine

HCID 8083Morpholine

HCID 53244122,6-Dichloropurine

Product 1

HCID 32746034-(2-chloro-9H-purin-6-yl)morpholine

Procedure

As shown in Scheme 4, a purine compound of the invention can be prepared by using commercially-available 2,6-dichloro-7H-purine as a starting material. The two chloro groups can be displaced by various substituents. More specifically, for example, the first chloro group (e.g., at position 6) can be displaced by morpholine to give a 2-chloro-6-(morpholin-4-yl)-7H-purine. The second chloro group can then be displaced by a nucleophile, e.g., hydrazine, and the primary amine of the coupled hydrazine moiety can be further reacted with an aldehyde, e.g., 3-methyl-6-methoxy-benzaldehyde, 3-methyl-6-amino-benzaldehyde, or 1H-indole carbaldehyde to form a hydrazone linkage.

Sources & evidence

ORD record: ord-1c22abd00c974bca8d7adea265b36845
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615552B2

Reaction notes

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