Hydrogen Bromide → HCID 86267406, compound

HRID 709983Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([O:10]C)[C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=4)[CH:20]=3)=[C:14]([CH3:32])[N:13]=2)=[CH:6][N:5]=1)[CH3:2].Br>>[CH2:1]([NH:3][C:4]1[NH:9][C:8](=[O:10])[C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=4)[CH:20]=3)=[C:14]([CH3:32])[N:13]=2)=[CH:6][N:5]=1)[CH3:2]

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 90416753HCID 90416753, compound

Product 1

HCID 86267406HCID 86267406, compoundYield 73%

Procedure

Using the procedure of Example 1, N-ethyl-4-methoxy-5-(6-methyl-5-((6′-methyl-[2,3′-bipyridin]-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.13 g, 0.3 mmol) and 48% HBr (0.66 mL, 12 mmol) were combined to afford 2-(ethylamino)-5-(6-methyl-5-((6′-methyl-[2,3′-bipyridin]-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one as a white solid (0.09 g, 73%). 1H NMR (400 MHz, DMSO-d6): δ 11.08 (s, 1H), 9.10 (s, 1H), 8.68 (s, 1H), 8.53 (d, J=5.7 Hz, 1H), 8.28 (d, J=8.3 Hz, 2H), 7.62 (s, 1H), 7.54 (d, J=8.7 Hz, 1H), 7.34 (d, J=8.2 Hz, 1H), 6.82 (br s, 1H), 6.78 (d, J=5.7 Hz, 1H), 3.35-3.32 (m, 2H), 2.50 (s, 3H), 2.35 (s, 3H), 1.12 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 415.2 (M+H+).

Sources & evidence

ORD record: ord-7b58e2776f0b40479fdde850e945409d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181223B2

Reaction notes

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