2,5-Pyridinediamine → N5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)pyridin-2-YL)pyridine-2,5-diamine

HRID 1621419Notes

Reaction equation

HRID 1621419 reaction equation
F[C:2]1[C:7]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH2:15])[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][N:18]=1>>[NH2:15][C:10]1[N:11]=[C:12]([CH3:14])[N:13]=[C:8]([C:7]2[C:2]([NH:23][C:20]3[CH:21]=[CH:22][C:17]([NH2:16])=[N:18][CH:19]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[N:9]=1

Participants

3

Reactant 2

HCID 203142,5-PyridinediamineHCID 665998524-(2-Fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 49785082N5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)pyridin-2-YL)pyridine-2,5-diamine

Procedure

The title compound was prepared following the procedure of Example 49, utilizing 4-(2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine and 2,5-diaminopyridine (Aldrich). LCMS (API-ES) m/z 295 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.52 (s, 1H); 8.75 (d, J=7.83 Hz, 1H); 8.74 (dt, J=7.83, 1.08 Hz, 1H); 8.34 (d, J=2.74 Hz, 1H); 8.27 (d, J=1.76 Hz, 1H); 8.26 (d, J=2.15 Hz, 1H); 7.87 (d, J=8.80 Hz, 1H); 7.88 (dt, J=9.00, 1.08 Hz, 1H); 7.68 (br. s., 1H); 6.83 (dd, J=7.82, 4.70 Hz, 1H); 6.62 (d, J=8.80 Hz, 1H); 2.42 (s, 3H).

Sources & evidence

ORD record
ord-5b624e8eb0a843fbad6aee3f4dece5ca
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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