4-Bromo-4'-methylbenzophenone → HCID 10272637, compound

HRID 1392980Notes

Reaction equation

HRID 1392980 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.Br[C:18]1[CH:32]=[CH:31][C:21]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)=[O:23])=[CH:20][CH:19]=1>>[CH3:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]([C:21]2[CH:31]=[CH:32][C:18]([NH:1][C:2]3[N:7]=[C:6]([C:8]4[N:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:11]5=[N:10][CH:9]=4)[CH:5]=[CH:4][N:3]=3)=[CH:19][CH:20]=2)=[O:23])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 27570564-Bromo-4'-methylbenzophenoneHCID 691978644-(Imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine

Product 1

HCID 10272637HCID 10272637, compoundYield 17%

Procedure

The title compound was prepared from 2-amino-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidine and 4-bromo4′-methylbenzophenone following the general method of Example 2. The crude product was purified by column chromatography on silica gel using chloroform/ethanol, 98:2, as the eluent affording 52 mg (17% yield) of the title compound as a yellow solid: mp 238.9-239.2° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.15-10.13 (m, 2 H), 8.64 (s, 1 H), 8.50 (d, J=5.3 Hz, 1 H), 7.96 (d, J=8.5 Hz, 2 H), 7.79-7.74 (m, 3 H), 7.63 (d, J=7.8 Hz, 2 H), 7.53-7.49 (m, 2 H), 7.35 (d, J=7.7 Hz, 2 H), 7.16 (t, J=6.8 Hz, 1 H), 2.40 (s, 3 H); 13C NMR (400 MHz, DMSO-d6) δ 194.4, 159.4, 157.7, 157.4, 148.4, 145.1, 142.7, 139.4, 135.5, 131.5, 130.1, 129.9, 129.8, 129.3, 127.5, 121.3, 118.2, 117.8, 114.2, 108.6, 21.5; MS (TSP) m/z 406 (M+1).

Workup

  1. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-48008c41dd20405cb0529cd9a52265a1
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

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