1H-Indazol-6-amine → 6-chloro-N4-(1H-indazol-6-yl)-pyrimidine-2,4-diamine

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:10])[CH:8]=2)[CH:3]=[N:2]1.[Cl:11][C:12]1[N:17]=[C:16]([NH2:18])[N:15]=[C:14](NC2C=CC(Cl)=CC=2)[CH:13]=1>>[Cl:11][C:12]1[N:17]=[C:16]([NH2:18])[N:15]=[C:14]([NH:10][C:7]2[CH:8]=[C:9]3[C:4]([CH:3]=[N:2][NH:1]3)=[CH:5][CH:6]=2)[CH:13]=1

Participants

Reactant 2

HCID 814231H-Indazol-6-amine

HCID 14842856-chloro-4-N-(4-chlorophenyl)pyrimidine-2,4-diamine

Product 1

HCID 860043126-chloro-N*4*-(1H-indazol-6-yl)-pyrimidine-2,4-diamineYield 42%

Procedure

Using 1H-indazol-6-yl-amine in place of 4-chloro-phenylamine in the method described in Example 2 for the synthesis of 6-chloro-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine provided 6-chloro-N*4*-(1H-indazol-6-yl)-pyrimidine-2,4-diamine (42% yield).

Sources & evidence

ORD record: ord-9291d5801b7548cbaa3c9701328ebf7b
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Reaction notes

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