2-Bromothiophene-3-carbonitrile → 2-{4-[7-(1-Methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidin-3-yl]pyrimidin-2-yl}thiophene-3-carbonitrile
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.CC1(C)C(C)(C)OB([C:36]2[S:37][CH:38]=[CH:39][C:40]=2[C:41]#[N:42])O1.BrC1SC=CC=1C#N>>[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:36]4[S:37][CH:38]=[CH:39][C:40]=4[C:41]#[N:42])[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
4
Reactant 3
Product 1
Procedure
3-(2-Chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine was reacted with 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)thiophene-3-carbonitrile (synthesised from 2-bromothiophene-3-carbonitrile following the procedure in Example 21) by the method of Example 35 to afford 2-{4-[7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidin-3-yl]pyrimidin-2-yl}thiophene-3-carbonitrile as a white solid: δH (400 MHz, CDCl3) 0.67 (6H, q, J 8.1), 0.99 (9H, t, J 8.0), 1.71 (6H, s), 7.66 (2H, m), 7.97 (1H, d, J 5.5), 8.51 (1H, s), 8.79 (1H, d, J 5.5), 9.71 (1H, m), 10.34 (1H, d, J 7.0); m/z (ES+) 477 (M++H).
Sources & evidence
- ORD record
- ord-877f2afd5ff442aaa7b35c82f22dec51
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07030128B2
Reaction notes
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