(3-Amino-4-methylphenyl)boronic acid → 5-[2-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]-2-methylaniline

HRID 970004Notes

Reaction equation

HRID 970004 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[N:6][CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[CH3:24]>>[N:11]12[CH2:16][CH2:15][CH:14]([CH2:13][CH2:12]1)[CH:9]([O:8][C:5]1[N:4]=[CH:3][C:2]([C:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[C:18]([CH:19]=3)[NH2:17])=[CH:7][N:6]=1)[CH2:10]2

Participants

3

Reactant 2

HCID 2737803(3-Amino-4-methylphenyl)boronic acidHCID 210726093-((5-Bromopyrimidin-2-yl)oxy)quinuclidine

Product 1

HCID 112553565-[2-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]-2-methylaniline

Procedure

The product of Example 18A (160 mg, 0.57 mmol) was treated with 3-amino-4-methyl-phenylboronic acid (Lancaster, 302 mg, 2.0 mmol) according to the procedure of Example 1B. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.1) as solid (45 mg, yield, 26%). 1H NMR (300 MHz, MeOH-d4) δ 1.48-1.62 (m, 1H), 1.65-1.90 (m, 2H), 2.01-2.16 (m, 1H), 2.19 (s, 3H), 2.22-2.29 (m, 1H), 2.74-3.01 (m, 5H), 3.36-3.47 (m, 1H), 5.12-5.20 (m, 1H), 6.86 (dd, J=7.51.7 Hz, 1H), 6.95 (d, J=1.7 Hz, 1H), 7.10 (d, J=8.1 Hz, 1H), 8.73 (s, 2H) ppm. MS (DCl/NH3) m/z 311 (M+H)+.

Workup

  1. customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.1) as solid (45 mg, yield, 26%)

Sources & evidence

ORD record
ord-f2c7aab7ae5b455ebc8e562f61964bc6
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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