4-(Imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine → HCID 10203313, compound

HRID 1392982Notes

Reaction equation

HRID 1392982 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:34]=[CH:33][C:21]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][CH3:32])[CH:25]=2)=[O:23])=[CH:20][CH:19]=1>>[CH2:31]([O:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[C:22]([C:21]1[CH:20]=[CH:19][C:18]([NH:1][C:2]2[N:7]=[C:6]([C:8]3[N:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]4=[N:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)=[CH:34][CH:33]=1)=[O:23])[CH3:32]

Participants

3

Reactant 2

HCID 691978644-(Imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amineHCID 69198022HCID 69198022, compound

Product 1

HCID 10203313HCID 10203313, compoundYield 48%

Procedure

The title compound was prepared from 2-amino-4-(imidazo-[1,2-a]pyridin-3-yl)pyrimidine and 4-bromo-3′-ethoxybenzophenone 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 0.11 g (48% yield) of the title compound as a yellow solid: mp 197.3-197.5° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.21 (s, 1 H), 10.17 (d, J=6.8 Hz, 1 H), 8.68 (s, 1 H), 8.53 (d, J=5.4 Hz, 1 H), 8.00 (d, J=8.5 Hz, 2 H), 7.82-7.79 (m, 3 H), 7.55-7.51 (m, 2 H), 7.47 (t, J=8.2 Hz, 1 H), 7.28 (d, J=7.5 Hz, 1 H), 7.23-7.17 (m, 3 H), 4.10 (q, J=6.8 Hz, 2 H), 1.36 (t, J=6.9 Hz, 3 H); 13C NMR (400 MHz, DMSO-d6) δ 194.4, 159.4, 158.7, 157.6, 157.4, 148.4, 145.4, 139.7, 139.4, 131.6, 129.9, 129.8, 129.8, 127.5, 22.0, 121.3, 118.6, 118.2, 117.8, 114.8, 114.2, 108.6, 63.6, 15.0; MS (ESP) m/z 436 (M+1).

Workup

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

Sources & evidence

ORD record
ord-f9989b56829a4e8aa20003c11d8a1bf5
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

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