Hydrogen Bromide → HCID 86267823, compound

HRID 709998Notes

Reaction equation

HRID 709998 reaction equation
[CH:1]([NH:4][C:5]1[N:10]=[C:9]([O:11]C)[C:8]([C:13]2[CH:18]=[C:17]([CH3:19])[C:16]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]4[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=4)[CH:22]=3)=[CH:15][N:14]=2)=[CH:7][N:6]=1)([CH3:3])[CH3:2].Br>C(O)(=O)C>[CH:1]([NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([C:13]2[CH:18]=[C:17]([CH3:19])[C:16]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]4[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=4)[CH:22]=3)=[CH:15][N:14]=2)=[CH:7][N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 90416084HCID 90416084, compound

Product 1

HCID 86267823HCID 86267823, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Using the procedure of Example 3, N-isopropyl-4-methoxy-5-(4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.053 g, 0.12 mmol) and HBr (0.2 mL) were combined in acetic acid (3 mL) to afford 2-(isopropylamino)-5-(4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (0.03 g, 59%). 1H NMR (400 MHz, DMSO-d6): δ 10.86 (s, 1H), 8.65 (s, 1H), 8.34 (m, 2H), 8.30 (s, 1H), 8.25 (s, 1H), 7.96 (s, 1H), 7.21 (d, J=2.4 Hz, 1H), 6.63 (br s, 1H), 6.58 (dd, J=5.7, 2.4 Hz, 1H), 4.09-4.07 (m, 1H), 3.84 (s, 3H), 2.14 (s, 3H), 1.16 (d, J=6.5 Hz, 6H); MS (ESI) m/z: 418.2 (M+H+).

Sources & evidence

ORD record
ord-a191a3efb3434e79a3a65d9d9640e7d2
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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