Potassium tert-butoxide → 2-[4-(4,5-Dihydro-1H-pyrazol-4-ylcarbonyl)anilino]-4-(imidazo-[1,2-a]-pyridin-3-yl)pyrimidine

HRID 1392987Notes

Reaction equation

HRID 1392987 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:23]=[CH:22][C:21]([C:24]([C:26]2[CH:27]=[N:28][NH:29][CH:30]=2)=[O:25])=[CH:20][CH:19]=1.CC(C)([O-])C.[K+]>>[NH:29]1[CH2:30][CH:26]([C:24]([C:21]2[CH:22]=[CH:23][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:25])[CH:27]=[N:28]1

Participants

4

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 691978644-(Imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amineHCID 69200129(4-bromophenyl)(1H-pyrazol-4-yl)methanone

Product 1

HCID 101104922-[4-(4,5-Dihydro-1H-pyrazol-4-ylcarbonyl)anilino]-4-(imidazo-[1,2-a]-pyridin-3-yl)pyrimidineYield 8%

Procedure

The title compound was prepared from 2-amino-4-(imidazo-[1,2-a]pyridin-3-yl)pyrimidine and (4-bromophenyl)(1H-pyrazol-4-yl)methanone following the general method of Example 1 using potassium tert-butoxide as the base. The crude product was purified by column chromatography on silica gel using chloroform/ethanol, 95:5, as the eluent affording 0.020 g (8% yield) of the title compound as a yellow solid: mp (decomp.) 229-232° C.; MS (TSP) m/z 382 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 10.27 (d, J=6.9 Hz, 1 H), 10.21 (s, 1 H), 8.76 (s, 1 H), 8.62 (d, J=5.4 Hz, 1 H), 8.30 (br s 2H), 8.03 (m, 5 H), 7.89 (m, 1 H), 7.62 (m, 2 H), 7.29 (m, 1 H).

Workup

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

Sources & evidence

ORD record
ord-e65b7f2f77434131a0445f23a3af4f01
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

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