2-Cyanopyrimidine-5-boronic acid pinacol ester → 5-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}pyrimidine-2-carbonitrile

HRID 2090377Notes

Reaction equation

HRID 2090377 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH3:26])[N:8]([C:12]3[CH:17]=[C:16]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[N:15]=[C:14]([NH2:25])[N:13]=3)[CH2:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[N:37][C:38]([C:41]#[N:42])=[N:39][CH:40]=2)O1>>[NH2:25][C:14]1[N:13]=[C:12]([N:8]2[CH:7]([CH3:26])[CH2:6][C:5]3[C:10](=[CH:11][C:2]([C:35]4[CH:36]=[N:37][C:38]([C:41]#[N:42])=[N:39][CH:40]=4)=[CH:3][CH:4]=3)[CH2:9]2)[CH:17]=[C:16]([N:18]2[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]2)[N:15]=1

Participants

3

Reactant 2

HCID 164142762-Cyanopyrimidine-5-boronic acid pinacol esterHCID 594023174-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

Product 1

HCID 594023385-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}pyrimidine-2-carbonitrile

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 50A starting from 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (Peak 2, Example 49, Step 7) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-carbonitrile (Frontier, Cat. No. C2065). LCMS (M+H)+: m/z=442.2.

Workup

  1. customThis compound was prepared
  2. customthose described for the synthesis of Example 50A

Sources & evidence

ORD record
ord-57669db759784d45974fbd1a6531b99d
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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