2-Methylpyridine-5-boronic acid → 5-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-N-(6-methoxypyridin-3-YL)-6'-methyl-3,3'-bipyridin-6-amine

HRID 1621758Notes

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.[CH3:43][C:44]1[N:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1>>[NH2:24][C:19]1[N:20]=[C:21]([CH3:23])[N:22]=[C:17]([C:4]2[CH:3]=[C:2]([C:47]3[CH:48]=[N:49][C:44]([CH3:43])=[CH:45][CH:46]=3)[CH:7]=[N:6][C:5]=2[NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[N:18]=1

Participants

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acid

HCID 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 595482745-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-N-(6-methoxypyridin-3-YL)-6'-methyl-3,3'-bipyridin-6-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 6-methylpyridin-3-ylboronic acid (40.5 mg, 0.296 mmol) (Frontier Scientific), and was isolated as a yellow crystalline solid (56%). m/z (ESI, +ve ion) 401.0 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.85 (1H, s); 9.03 (1H, d, J=2.7 Hz); 8.77 (1H, d, J=2.2 Hz); 8.67 (1H, d, J=2.5 Hz); 8.56 (1H, d, J=2.7 Hz); 8.20 (1H, dd, J=8.8, 2.7 Hz); 7.99 (1H, dd, J=8.1, 2.2 Hz); 7.91 (1H, br. s.); 7.77 (1H, br. s.); 7.38 (1H, d, J=8.2 Hz); 6.85 (1H, d, J=8.8 Hz); 3.86 (3H, s); 2.52 (3H, s); 2.46 (3H, s).

Sources & evidence

ORD record: ord-f492e1862202402fb8be378a908b30ce
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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