2-(2-Phenyldiazenyl)propanedinitrile → 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)-5-(phenyldiazenyl)pyrimidine-4,6-diamine

HRID 2174293Notes

Reaction equation

HRID 2174293 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15](=[NH:17])[NH2:16])=[N:6]1.[C:22]1([N:28]=[N:29][CH:30]([C:33]#[N:34])[C:31]#[N:32])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]2[N:16]=[C:31]([NH2:32])[C:30]([N:29]=[N:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:33]([NH2:34])[N:17]=2)=[N:6]1

Participants

4

Reactant 2

HCID 223472-(2-Phenyldiazenyl)propanedinitrileHCID 690942961-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboximidamide

Product 1

HCID 690940742-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)-5-(phenyldiazenyl)pyrimidine-4,6-diamineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboximidamide (Intermediate-6, 0.38 mmol) and 2-(phenyldiazenyl)malononitrile (1 equiv) in ethanol (6 mL) in a sealed tube was heated at 110° C. for 2 h. The reaction was conc. to afford 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)-5-(phenyldiazenyl)pyrimidine-4,6-diamine as an orange solid (>99% yield).

Sources & evidence

ORD record
ord-39917d0df3a64197bc0d1c20a9715588
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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