4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 4-(2-(6-Methoxypyridin-3-ylamino)-5-(1H-pyrazol-4-YL)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

HRID 1621757Notes

Reaction equation

HRID 1621757 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:17]2[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:18]=2)[C:5]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:51]2[CH:52]=[N:53][NH:54][CH:55]=2)O1>>[CH3:16][O:15][C:12]1[N:11]=[CH:10][C:9]([NH:8][C:5]2[C:4]([C:17]3[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=3)=[CH:3][C:2]([C:51]3[CH:52]=[N:53][NH:54][CH:55]=3)=[CH:7][N:6]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 666119674-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 497854404-(2-(6-Methoxypyridin-3-ylamino)-5-(1H-pyrazol-4-YL)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Procedure

The title compound was prepared in an analogous manner to that described in Example 247 using 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Strem Chemicals), and was isolated as an orange amorphous solid (95%). m/z (ESI, +ve ion) 376.1 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 12.98 (1H, br. s.); 11.70 (1H, s); 8.89 (1H, br. s.); 8.59 (2H, br. s.); 8.17 (2H, br. s.); 7.87 (2H, br. s.); 7.74 (1H, br s.); 6.84 (1H, s); 3.85 (3H, s); 2.46 (3H, br. s.).

Sources & evidence

ORD record
ord-ac16826d47f24e61a01a092e51eabbd2
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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