3-(Diethylboryl)pyridine → 7-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(pyridin-3-yl)pyrimidin-4-yl]imidazo[1,2-alpha]pyrimidine

HRID 1796053Notes

Reaction equation

HRID 1796053 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([CH3:27])([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.C(B(CC)[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)C>>[CH3:18][C:17]([C:15]1[CH:14]=[CH:13][N:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[N:7]=3)=[CH:9][N:10]=[C:11]2[N:16]=1)([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:27]

Participants

3

Reactant 2

HCID 6428513-(Diethylboryl)pyridineHCID 878895493-(2-Chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)-imidazo[1,2-alpha]pyrimidine

Product 1

HCID 695603487-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(pyridin-3-yl)pyrimidin-4-yl]imidazo[1,2-alpha]pyrimidine

Procedure

3-(2-Chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine was reacted with diethyl(3-pyridyl)borane by the method of Example 35 to afford 7-(1-methyl-1-triethylsilanyloxyethyl)-3-[2-(pyridin-3-yl)pyrimidin-4-yl]imidazo[1,2-α]pyrimidine as a white solid: δH (400 MHz, CDCl3) 0.73 (6H, q, J 8.1), 1.01 (9H, t, J 8.0), 1.72 (6H, s), 7.46-7.53 (2H, m), 7.61 (1H, d, J 5.5), 7.67 (1H, d, J 7.0), 8.52 (1H, s), 8.72-8.79 (2H, m), 9.71 (1H, m), 10.24 (1H, d, J 7.0); m/z (ES+) 447 (M++H).

Sources & evidence

ORD record
ord-1578c2da690942f0a5b05fd6fa325dac
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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