Hydrogen Bromide → HCID 86267825, compound

HRID 710001Notes

Reaction equation

HRID 710001 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:18]=3)=[CH:11][N:10]=2)=[CH:7][N:6]=[C:5]([N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[N:4]=1.Br>C(O)(=O)C>[CH3:15][C:13]1[C:12]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]3[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=3)[CH:18]=2)=[CH:11][N:10]=[C:9]([C:8]2[C:3](=[O:2])[NH:4][C:5]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[N:6][CH:7]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 90417260HCID 90417260, compound

Product 1

HCID 86267825HCID 86267825, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-methoxy-5-(4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-(pyrrolidin-1-yl)pyrimidine (0.19 g, 0.43 mmol) in acetic acid (2.5 mL) was treated with HBr (48%, 0.10 mL, 1.8 mmol) and heated at 90° C. for 16 h. The mixture was poured onto ice (10 g), neutralized with satd. NaHCO3, and the resulting solid was collected by filtration, washed with water and MeCN and dried to afford 5-(4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-(pyrrolidin-1-yl)pyrimidin-4(3H)-one (0.11 g, 58%). 1H NMR (400 MHz, DMSO-d6): δ 11.22 (bs, 1H), 8.68 (s, 1H), 8.38 (s, 1H), 8.34 (d, J=5.7 Hz, 1H), 8.30 (d, J=1.3 Hz, 1H), 8.26 (s, 1H), 7.96 (s, 1H), 7.22 (d, J=2.4 Hz, 1H), 6.60-6.58 (m, 1H), 3.84 (s, 3H), 3.50 (bs, 4H), 2.15 (s, 3H), 1.91 (bs, 4H); MS (ESI) m/z: 430.2 (M+H+).

Workup

  1. additionThe mixture was poured onto ice (10 g)
  2. filtrationNaHCO3, and the resulting solid was collected by filtration
  3. washwashed with water and MeCN
  4. customdried

Sources & evidence

ORD record
ord-3140457d48074d39a4a286686bbf1b35
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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